Investigations on the question of multiple mechanisms in the cope rearrangement

The possible occurrence of the ionic Cope rearrangement, and other non-concerted mechanisms is discussed. The synthesis of 2 - (1 - ethyl - 1 - propenyl) -2- (3 - p - methoxyphenylallyl)malononitrile (1b) and its clean thermal 1,3 rearrangement to (1 - ethyl - 5 - p - methoxyphenyl - 2 - methyl - 4 - pentenylidene)malononitrile (4) are reported. This result contrasts with the rearrangement of 2 - (1,1 - dideuterioallyl) - 2 -(1 - ethyl - 1 - propenyl)malononitrile (1c) which isomerizes cleanly in a 3,3 rearrangement. Rearrangement of 2 - (1 - cyclohexenyl) - 2 - (3 - p - methoxyphenylallyl)malononitrile (11), however, leads sluggishly to [2 - (p - methoxy - α - vinylbenzyl)cyclohexylidene]malononitrile (19) (3,3 shift) and rearrangement of 2 - (1 - isopropyl - 2 - methyl - 1 - propenyl) - 2 -(3 - p - methoxyphenylallyl)malononitrile (12) leads, also slowly, to (1 - isopropyl - 5-p- methoxyphenyl - 2,2 - dimethyl - 4 - pentenylidene)malononitrile (14) (1,3 shift). Rearrangement of 1b in the presence of sodium borohydride allows interception of the proposed ionic intermediates and isolation of 2 - (1 - ethylpropylidene)malononitrile (5) and anethole (21c). Ion trapping experiments also gave positive results in the 3,3 rearrangement of 11. These results are discussed in terms of the ionic Cope rearrangement.     

Sesquiterpenoids of the Sponge Dysidea fragilis of the North-Brittany Sea

The title sponge is shown to contain eight new sesquiterpenoids for which a common, unusual biogenetic origin is postulated. The compounds are shown to be: (–)-(1R*,4R*)-3-(3′-furyl)methyl-2-p-menthen-7-yl acetate ((–)- 8b ); two diols separated as the monoacetates (–)-(1S*,4R*)-3-(3′-furyl)methyl-l-hydroxy-2-p-menthen-7-yl acetate ((–)- 13a ) and the (–)-(1R*,4R*)-epimer (–)- 13b , the two C(4)-epimeric 4-ethoxy-3-(1′(7′),2′-p-menthadien-3′-yl)methyl-2-buten-4-olides ((+)- 14a and (–)- 14b ), (–)-3-(3′-furyl)methyl-7-nor-2-p-menthen-l-one ((–)- 11 ), (–)-(3Z)-1-(3′-furyl)-4,8-dimethylnona-3, 7-dien-2-yl acetate ((–)- 17 ), and (+)-3-(5′,7′-seco-2′(10′)-pinen-7′-yl)methylfuran ((+)- 15 ).     

Isolation and identification of the anti-isohumulones and the anti-acetylhumulinic acids

The anti-isohumulones [5-(3-methylbutanoyl)-2-(3-methylbut-2-enyl)-4-hydroxy-4-(4-methylpent-3-enoyl)-cyclopentane-1,3-diones] and the anti-acetylhumulinic acids [5-(3-methylbutanoyl)-2-(3-methylbut-2-enyl)-4-ethanoyl-4-hydroxy-cyclopentane 1,3-diones] have been isolated from an isomerisation reaction mixture of humulone [2-(3-methylbutanoyl)-4,6-di(3-methylbut-2-enyl)-6-hydroxy-cyclohexane-l,3,5-trione] by counter-current distribution and identified by spectroscopic techniques. The formation mechanism is presented and the stereochemical consequences are discussed. The anti-isohumulones are the most bitter hop compounds presently known.     

Kinetics of the unimolecular decomposition of the 2-chloroallyl radical

The thermal decomposition of the 2-chloroallyl radical, CH(2)CClCH(2) --> CH(2)CCH(2) + Cl (1), was studied using the laser photolysis/photoionization mass spectrometry technique. Rate constants were determined in time-resolved experiments as a function of temperature (720-840 K) and bath gas density ([He] = (3-12) x 10(16), [N(2)] = 6 x 10(16) molecule cm(-3)). C(3)H(4) was observed as a primary product of reaction 1. The rate constants of reaction 1 are in the falloff, close to the low-pressure limit, under the conditions of the experiments. The potential energy surface (PES) of reaction 1 was studied using a variety of quantum chemical methods. The results of the study indicate that the minimum energy path of the CH(2)CClCH(2) dissociation proceeds through a PES plateau corresponding to a weakly bound Cl-C(3)H(4) complex; a PES saddle point exists between the equilibrium CH(2)CClCH(2) structure and the Cl-C(3)H(4) complex. The results of quantum chemical calculations, the rate constant values obtained in the experimental study, and literature data on the reverse reaction of addition of Cl to allene were used to create a model of reactions 1 and -1. The experimental dependences of the rate constants on temperature and pressure were reproduced in RRKM/master equation calculations. The reaction model provides expressions for the temperature dependences of the high-pressure-limit and the low-pressure-limit rate constants and the falloff broadening factors (at T = 300-1600 K): k(infinity)(1) = 1.45 x 10(20)T(-1.75) exp(-19609 K/T) s(-1), k(infinity)(-)(1) = 8.94 x 10(-10)T(-0.40) exp(481 K/T) cm(3) molecule(-1) s(-1), k(1)(0)(He) = 5.01 x 10(-32)T(-12.02) exp(-22788 K/T) cm(3) molecule(-1) s(-1), k(1)(0)(N(2)) = 2.50 x 10(-32)T(-11.92) exp(-22756 K/T) cm(3) molecule(-1) s(-1), F(cent)(He) = 0.46 exp(-T/1001 K) + 0.54 exp(-T/996 K) + exp(-4008 K/T), and F(cent)(N(2)) = 0.37 exp(-T/2017 K) + 0.63 exp(-T/142 K) + exp(-4812 K/T). The experimental data are not sufficient to specify all the parameters of the model; consequently, some of the model parameters were obtained from quantum chemical calculations and from analogy with other reactions of radical decomposition. Thus, the parametrization is most reliable under conditions close to those used in the experiments.     

Influence of chirality of the preceding acyl moiety on the cis/trans ratio of the proline peptide bond

We report that the cis/trans ratio of the proline peptide bond can be strongly influenced by the chirality of the acyl residue preceding proline. Acyl moieties derived from (2S)-2,6-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid (8) and (2R)-3-methoxy-2-methyl-2-(4-methyl-2-nitrophenoxy)-3-oxopropanoic acid (5) in acyl-Pro molecules influence isomerization of the proline peptide bond constraining the omega dihedral angle to the trans orientation. Structures of benzyl (2S)-1-([(2S)-2,6-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]carbonyl)-2-pyrrolidinecarboxylate (3) derived from 2D (1)H NMR conformational analysis and crystallographic data exhibit only the trans conformation of proline peptide bond. On the other hand the diastereomer 4, which contains an (R) acyl moiety, exhibits two sets of signals in (1)H NMR spectra. The signals were assigned to trans (72%) and cis (28%) conformers. Crystallographic analysis of 4 showed that only the cis conformation is present in the crystalline state. The (1)H NMR chemical shift pattern of three sets of signals observed in 2 was observed also in benzyl (2S)-1-[(2R/S)-3-methoxy-2-methyl-2-(4-methyl-2-nitrophenoxy)-3-oxopropanoyl]-2-pyrrolidinecarboxylate. (R)-Carboxylic acid 5, after coupling with (S)-ProOBn, yielded benzyl (2S)-1-[(2R)-3-methoxy-2-methyl-2-(4-methyl-2-nitrophenoxy)-3-oxopropanoyl]-2-pyrrolidinecarboxylate (6), which in DMSO-d(6) exhibited only the trans conformation of the proline peptide bond. These results suggest that in these particular cases acyl-Pro peptide bond isomerization is strongly influenced by the stereochemistry of the acyl residue preceding proline. (2S)-2,6-Dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid (8) and (2R)-3-methoxy-2-methyl-2-(4-methyl-2-nitrophenoxy)-3-oxopropanoic acid (5) are promising chiral peptidomimetic building blocks that can be used as acyl moieties to force the proline peptide bond into the trans conformation in a variety of acyl-Pro molecules.     

Experimental correlation between the pKa value of sulfonphthaleins with the nature of the substituents groups

This work presents the results obtained from a spectrophotometry study performed on some indicators of the sulfonphtaleins like phenol red (PR), thymol blue (TB), bromothymol blue (BTB), xylenol orange (XO) and methylthymol blue (MTB). During the first stage the acidity constants of some of the indicators were determined using the data from spectrophotometry, potentiometry and with the use of the software SQUAD. These were as follows: for the equilibrium 2H+BTB<-->H(2)BTB, log beta(2)=15.069+/-0.046 and for H+BTB<-->HBTB, log beta(1)=8.311+/-0.044. For the XO and the MTB five values were calculated for each, namely, for MTB: log beta(5)=42.035, log beta(4)=38.567+/-0.058, log beta(3)=32.257+/-0.057, log beta(2)=23.785+/-0.057, and log beta(1)=12.974+/-0.045 while for XO: log beta(5)=40.120+/-0.102, log beta(4)=35.158+/-0.062, log beta(3)=29.102+/-0.053, log beta(2)=21.237+/-0.044, and log beta(1)=11.682+/-0.044. During the second stage, a study was conducted on the effect of the substituents present in the indicators to determine the effect of different functional groups on the pK(a) value corresponding to the last indicator's dissociation.     

Final elucidation of the absolute configuration of the signal metabolite hormaomycin

The complete absolute configuration of hormaomycin 1 a has been established by HPLC and HPLC/MS experiments with appropriately derivatized 4-propylprolines, (2S,4S)-6 and (2R,4R)-6, as well as 4-(Z)-propenylprolines, cis-5 and trans-5, and also feeding experiments with enantiomerically pure samples of the deuterium-labeled 3-(2'-nitrocyclopropyl)alanine, (2S)-3,3-[D2]15 and (2S)-2,2'-[D2]15, and 4-(Z)-propenylproline 2',4-[D2]-(2S,4R)-5. The latter five amino acids were prepared for the first time and allowed one to unequivocally assign the hitherto unknown absolute configurations of the last four stereocenters in hormaomycin 1 a. As a bonus, some new information about the biosynthesis of this molecule has also been gathered.     

Studies on the Extractive Constituents of the Nutmeg of Myristica Fragrans Houtt

From the hexane extractive of the nutmeg of Myristica fragrans Houtt, glyceryl trimyristate (1), myristicin (11), methyleugenol (12), elemicin (13), dehydrodiisoeugenol (9), 1-(3,4,5-trimethoxyphenyl)-2-(4-allyl-2,6-dimethoxyphenoxy)-propan-1-ol (4), 1-(3,4-methylenedioxyphenyl)-2-(4-allyl-2,6-dimethoxyphenoxy)-propan-1-ol (6), and a new compound 1-(3,4-dimethoxyphenyl)-2-(4-allyl-2,6-dimethoxyphenoxy) propan-1-ol (14) were isolated. The structure of compound (14) was determined to be an analogue of the β-0-4 ether type of dilignols.     

Cheletropic decomposition of cyclic nitrosoamines revisited: the nature of the transition states and a critical role of the ring strain

The cheletropic decompositions of 1-nitrosoaziridine (1), 1-nitroso-Delta(3)-pyrroline (2), 7-nitroso-7-azabicyclo[2.2. 1]hepta-2,5-diene (3), and 6-nitroso-6-azabicyclo[2.1.1]hexa-4-ene (4) have been studied theoretically using high level ab initio computations. Activation parameters of the decomposition of nitrosoaziridine 1 were obtained experimentally in heptane (DeltaH()(298) = 18.6 kcal mol(-)(1), DeltaS()(298) = -7.6 cal mol(-)(1) K(-)(1)) and methanol (20.3 kcal mol(-)(1), 0.3 cal mol(-)(1) K(-)(1)). Among employed theoretical methods (B3LYP, MP2, CCD, CCSD(T)//CCD), the B3LYP method in conjunction with 6-31+G, 6-311+G, and 6-311++G(3df,2pd) basis sets gives the best agreement with experimental data. It was found that typical N-nitrosoheterocycles 2-4 which have high N-N bond rotation barriers (>16 kcal mol(-)(1)) extrude nitrous oxide via a highly asynchronous transition state with a planar ring nitrogen atom. Nitrosoaziridine 1, with a low rotation barrier (<9 kcal mol(-)(1)) represents a special case. This compound can eliminate N(2)O via a low energy linear synperiplanar transition state (DeltaH()(298) = 20.6 kcal mol(-)(1), DeltaS()(298) = 2.5 cal mol(-)(1) K(-)(1)). Two higher energy transition states are also available. The B3LYP activation barriers of the cheletropic fragmentation of nitrosoheterocycles 2-4 decrease in the series: 2 (58 kcal mol(-)(1)) > 3 (18 kcal mol(-)(1)) > 4 (12) kcal mol(-)(1). The relative strain energies increase in the same order: 2 (0 kcal mol(-)(1)) < 3 (39 kcal mol(-)(1)) < 4 (52 kcal mol(-)(1)). Comparison of the relative energies of 2-4 and their transition states on a common scale where the energy of nitrosopyrroline 2 is assumed as reference indicates that the thermal stability of the cyclic nitrosoamines toward cheletropic decomposition is almost entirely determined by the ring strain.     

Synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from salmonella strasbourg

The pentasaccharide α - Tyv - (1→3) - β - d - Man - (1→4) - α - l - Rha - (1→3) - d - Gal - (4←1) -α - d - Glc 1, the repeating unit of the O-specific polysaccharide chain of the lipopolysaccharide from S. Strasbourg, was obtained by glycosylation of benzyl - 2,6 - di - O - benzyl - 4 - O - (2,3,4 - tri - O - benzyl - 6 - O - benzoyl - α - d - glucopyranosyl) - β - d - galactopyranoside with 1,2 - methylorthoacetyl - 3 - O - acetyl - 4- O - [3 - O - (2,4 - di - O - acetyl - 3, 6 - dideoxy,- α - d - arabino - hexopyranosyl) - 2,4,6 - tri - O - acetyl - β - d - mannopyranosyl] - β - l - rhamnopyranose 3 followed by removal of protecting groups. The structure of the synthetic pentasaccharide was proved by methylation analysis and ¹³C NMR.     

Increased enantioselectivity in the addition of diethylzinc to benzaldehyde by the use of chiral ligands containing the alpha-phenylethylamino group in combination with achiral ligands

Chiral ligands (S,S)-1, (S,S)-2, (S,S)-3, (S)-4, (S)-5, (S,S)-6, (S,S)-7, and (S,S)-8 turned out to be effective promoters in the enantioselective addition of diethylzinc to benzaldehyde. Interestingly, diamine (S,S)-3 and amino alcohols (S)-5 and (S,S)-7 induce the preferential formation of carbinol (R)-10 (unlike stereoinduction) whereas amido analogues (S,S)-2, (S)-4, and (S,S)-6 favor (S)-10 (like stereoinduction). Molecular modeling at the semiempirical PM3 level provided a reasonable interpretation based on conformational effects in the corresponding transition structures. Combinations of chiral ligands 1-8 with an achiral, flexible ligand (9) gave rise to an activated catalytic system that resulted in faster and higher yielding reactions. Furthermore, substantial increases in the observed enantiomeric excesses of product 10 confirmed the relevant role of achiral bis(sulfonamide) 9 as activator and "chiral environment amplifier".     

An investigation of the structure of the nitration products of 1-phenyl-5-styryltetrazole using the mass-spectrometric method

Depending on the reaction conditions, the nitration of 1-phenyl-5-styryltetrazole (I) with nitric acid and nitrating mixture give 1-(4-nitrophenyl)-5-styryltetrazole, 1-(4-nitrophenyl)-5-(4-nitrostyryltetrazole), and 1-(2,4-dinitrophenyl)-5-(4-nitrostyryl) tetrazole. The structures of the compounds obtained have been established by an analysis of their mass spectra and of the mass spectra of model compounds. The positions and sequences of entry of the nitro groups have been determined.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 558–563, April, 1980.     

磺酰氨基酸钛配合物对Diels-Alder反应的对映选择性催化作用

研究了对甲苯磺酰基-L-缬氨酸、对甲苯磺酰基-L-苯丙氨酸、对甲苯磺酰基-L-亮氨酸、对甲苯磺酰基-L-异亮氨酸、对甲苯磺酰基-L-脯氨酸、1-萘磺酰基-L-缬氨酸、1-萘磺酰基-L-苯丙氨酸、1-萘磺酰基-L-亮氨酸和1-萘磺酰基-L-异亮氨酸与钛的配合物对环戊二烯与丙烯酸甲酯的环加成反应的对映选择性催化作用。萘磺酰基氨基酸钛配合物的对映选择性比对甲苯磺酰基氨基酸钛配合物好,氨基酸与钛比为2:1时比1:1要好得多。1-萘磺酰基-L-异亮氨酸与钛的2:1配合物的对映选择性最好,e.e.值为56%。     

Increasing stability of the fullerenes with the number of carbon atoms: the experimental evidence

The values of the molar standard enthalpies of formation, Delta(f)H(o)(m)(C(76), cr) = (2705.6 +/- 37.7) kJ x mol(-1), Delta(f)H(o)(m)(C(78), cr) = (2766.5 +/- 36.7) kJ x mol(-1), and Delta(f)H(o)(m)(C(84), cr) = (2826.6 +/- 42.6) kJ x mol(-1), were determined from the energies of combustion, measured by microcombustion calorimetry on a high-purity sample of the D(2) isomer of fullerene C(76), as well as on a mixture of the two most abundant constitutional isomers of C(78) (C(2nu)-C(78) and D(3)-C(78)) and C(84) (D(2)-C(84), and D(2d)-C(84). These values, combined with the published data on the enthalpies of sublimation of each cluster, lead to the gas-phase enthalpies of formation, Delta(f)H(o)(m)(C(76), g) = (2911.6 +/- 37.9) kJ x mol(-1); Delta(f)H(o)(m)(C(78), g) = (2979.3 +/- 37.2) kJ x mol(-1), and Delta(f)H(o)(m)(C(84), (g)) = (3051.6 +/- 43.0) kJ x mol(-1), results that were found to compare well with those reported from density functional theory calculations. Values of enthalpies of atomization, strain energies, and the average C-C bond energy were also derived for each fullerene. A decreasing trend in the gas-phase enthalpy of formation and strain energy per carbon atom as the size of the cluster increases is found. This is the first experimental evidence that these fullerenes become more stable as they become larger. The derived experimental average C-C bond energy E(C-C) = 461.04 kJ x mol(-1) for fullerenes is close to the average bond energy E(C-C) = 462.8 kJ x mol(-1) for polycyclic aromatic hydrocarbons (PAHs).     

Theoretical study of the reactions of CF3OCHF2 with the hydroxyl radical and the chlorine atom.

Theoretical investigations are carried out on the reaction mechanism of the reactions of CF3OCHF2 (HFOC-125) with the OH radials and Cl atoms, as well as the heats of formation of CF3OCHF2 and CF3OCF2. The electronic structure information on the potential energy surface for each reaction is obtained at the B3LYP/6-311G(d,p) level, and energetic information is further refined by G3(MP2) theory. The direct dynamics calculation of the hydrogen abstraction reactions are also performed at the G3(MP2)//B3LYP/ 6-311G(d,p) level. The classical energy profile is corrected by interpolated single-point energies (ISPE) approach, incorporating the small-curvature tunnelling effect (SCT) calculated by the variational transition-state theory (VTST). The rate constants are in good agreement with the experimental data and are found to be k1 = 4.95 x 10(-30)T(5.40)exp(-347/T) and k2 = 1.86 x 10(-23)T(3.43)exp(-1579/T) cm3 molecule(-1)s(-1) over the temperature range 200-2000 K. The rate constants at 298 K for these two reactions are 3.38 x 10(-16) and 2.80 x 10(-17) cm3 molecule(-1)s(-1), respectively. Using group-balanced isodesmic reactions as working chemical reactions, the standard enthalpies of formation for CF3OCHF2 and CF3OCF2 are -312.3 +/- 1.0 and -257.3 +/- 1.0 kcalmol(-1), respectively, evaluated by G3(MP2) theory based on the B3LYP/6-311G(d,p) geometries. The theoretical studies provide rate constants of the title reactions and the enthalpies of the species, which are important parameters in determining the atmospheric lifetime and the feasible pathways for the loss of HFOC-125.     

On the hydrolysis of the dioxouranium(VI) ion in sulfate solutions

The formation of ternary UO2(2+)-(OH-)-SO4(2-) complexes has been studied at 25 degrees C in 3 M NaClO4 ionic medium by measurements with a glass electrode. The solutions had uranium concentrations between 0.3 and 30 mM, sulfate between 20 and 200 mM, and 1.66 < or = [SO4(2-)]/[U(VI)] < or = 300. The hydrogen ion concentration ranged from 10(-3) M to incipient precipitation of basic sulfates. This occurred, depending on the metal concentration, at [H+] between 10(-4) and 10(-5.3) M. In the interpretation of the data the stabilities of binary complexes were assumed from independent sources. The data could be explained with the mixed complexes and equilibria (beta(pqr)(3sigma) refers to pUO2(2+) + qH2O + rSO4(2-) <==> (UO2)p(OH)q(SO4)r(2p-q-2r) + qH+): logbeta222 = -2.94 +/- 0.03, logbeta341 = -9.82 +/- 0.06, logbeta211 = -0.30 +/- 0.09, logbeta212 = 1.09 +/- 0.09, logbeta351 = -15.04 +/- 0.09 and logbeta462 = -14.40 +/- 0.06. The fit could be improved by including UO2OH+ with logbeta110 = -5.1 +/- 0.1. The identity of the minor species remains, however, an open question.     

Studies on the Syntheses of the Side Chains of Brassinolide and Dolicholide

(4R,5S)-2,2-Dimethyl-4-(1',2'-dimethylpropyl)-5-(1'-bromoethyl)--1,3-dioxolane(15) with the side chain of brassinolide and (4R, 5S)--2, 2-dimethyl-4-(l'-methylene-2'-methylpropyl)-5-(1'-bromoethyl) 1,3-dioxolane(14) with the side chain of dolicholide were first synthesized through 11 and 10 stepes from D-mannitol respectively. All of the intermediates 7-13 were first synthesized too.     

Prediction of the existence of the N2H- molecular anion

We predict the existence of the N(2)H(-) anion from first principle calculations. We present the three-dimensional potential energy surface and the bound states of the N(2)H(-)/D(-) van der Waals anion. The electronic calculations were performed using state-of-the-art ab initio methods and the nuclear motions were solved using a quantum close-coupling scattering theory. A T-shaped equilibrium structure was found, with a well depth of 349.1 cm(-1), where 18 bound states have been located for N(2)H(-) and 25 for N(2)D(-) for total angular momentum J = 0. We also present the absorption spectra of the N(2)H(-) complex. This anion could be formed after low energy collisions between N(2) and H(-) through radiative association. The importance of this prediction in astrophysics and the possible use of N(2)H(-) as a tracer of N(2) and H(-) in the interstellar medium is discussed.     

Enantioselective synthesis of the pyrroloquinoline core of the martinellines

[equation--see text] The first enantioselective synthesis of the martinelline core (-)-3 is reported. The synthesis of (-)-3 from N-allyl-N-(benzyloxycarbonyl)-2-iodoaniline (12) proceeded in seven steps and 23% overall yield. In addition, the preparation of a carbocyclic model system is described.     

Ring-chain transformations with the participation of the C=N group

It was established that attack by the nucleophilic agent in the reactions of 2-(tert-butyl)-3-chloro-3-(p-chlorophenyl)isoindolinone with methylamine and ethylamine proceeds at C(₁) with subsequent ring opening and a new cyclization leading to 2-alkyl-3-(tert-butylamino)-3-(p-chlorophenyl)isoindolinones. A decrease in the nucleophilicity of the amine or an increase in the size of the substituent attached to the nitrogen atom leads to nucleophilic substitution at C(₃). Thermal isomerization of an aminolactam to an imino carboxylic acid amide was realized for the first time in the case of 2-(tert-butyl)-3-phenylamino-3-(p-chlorophenyl)isoindolinone. The structure of the 2-alkyl-3-amino-3-(p-chlorophenylisoindolinones was established by IR spectroscopy and acid hydrolysis to the corresponding 2-alkyl-3-hydroxy-3-(p-chlorophenyl)isoindolinones.See [1] for communication IV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1207–1210, September, 1976.