Reactivity of indanedioneketene dimer with amines

The highly reactive indanedioneketene 5, resulting from the thermal decomposition of phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone (lawsone, 4), in the absence of nucleophiles dimerizes to the corresponding tetraoxo spiro oxetanone 6 in quantitative yield. This oxetanone exhibits an interesting reactivity toward amines.     

Reactions of chloroalkyl-gem-dichlorocyclopropanes with amines

N-Alkylation of primary and secondary amines with monochloroalkyl-gem-dichlorocyclopropanes under conditions of thermal and microwave heating results in the corresponding amino-gem-dichlorocyclopropanes. With microwave irradiation heating, the reaction time has been decreased to 1 h, the yields of the amines containing gem-dichlorocyclopropane moiety being the same. Formation of the bicyclic amine in reaction of cis-2,3-dichloromethyl-gem-dichlorocyclopropane with primary amines under conditions of phasetransfer catalysis has been studied.     

Reactions of triethylborate with amines

Russian Chemical Bulletin -     

Reactions of a quintuply bonded chromium dimer with alkynes

Quintuply bonded [(H)L(iPr)Cr](2) reacts with alkynes RC≡CR (R = Me, Et, Ph, CF(3)) to form exclusively 1?:?1 adducts [(H)L(iPr)Cr](2)(RCCR). All products feature relatively short Cr-Cr distances (1.919-1.962 ?) and elongated C-C bonds (1.315-1.436 ?), consistent with [2+2] cycloaddition reactions. The hydrocarbon adducts are 4-membered metallacycles, the bridging alkynes of which are progressively skewed with respect to the Cr-Cr axis. In contrast, perfluoroalkyne adds across the metal ligand moiety.     

Reactions of boryloxymethyl- and hydroxymethylphosphines with amines

Conclusions 5-(Hydroxymethyl)-2,2,5-triphenyl-1,3,2,5-dioxaborataphosphoniarinane reacts with diphenylamine and o-aminobenzoic acid with the formation of 5-(aminomethyl)-2,2,5-triphenyl-1,3,2,5-dioxaborataphosphoniarinanes, whereas 1,5,3,7-diammoniadiphosphacyclooctanes are formed with m- and p-aminobenzoic acids. With o-aminobenzoic acid, hydroxymethylphosphines and hydroxymethylphosphonium salts give the corresponding aminomethylphosphines and aminomethylphosphonium salts.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1340–1343, June, 1989.Deceased.     

Reactions of sulfites with secondary amines

The interaction of diethylamine and morpholine with diphenyl, methyl phenyl, ethyl phenyl, and isopropyl phenyl sulfites was studied. It was established that two reactions, substitution and alkylation, can occur in parallel. Diphenyl sulfites react with amines to give only substitution products, while other sulfites react with substitution at the sulfur atom and with alkylation of the amines. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1395–1397, July, 1998.     

Reactions of primary amines with tetracyanoethylene

Primary amines, 3-triethoxysilylpropylamine, 3-silatranylpropylamine, and cyclohexylamine, react with tetracyanoethylene in acetonitrile at room temperature via addition at the cyano group to afford the corresponding amidines. N-Cyclohexyltricyanoacrylamidine exists as a mixture of two of the three possible isomers, while N-(3-triethoxysilylpropyl)tricyanoacrylamidine and N-(3-silatranylpropyl)tricyanoacrylamidine exist mainly as a single isomer containing NH₂ group. N-(3-Triethoxysilylpropyl)tricyanoacrylamidine was used to prepare gels and films.Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 9, 2004, pp. 1308–1314.Original Russian Text Copyright © 2004 by Ladilina, Semenov, Kurskii, Khorshev, Domrachev.     

Reactions of amines with bischloromethyltetramethyldisiloxane and its derivatives

Summary The reaction of bischloromethyltetramethyldisiloxane and its derivatives with mono- and di-amines was investigated, and it was shown that reaction proceeds with formation of cyclic compounds irrespective of the groups attached to the silicon atoms. Six new compounds were synthesized.     

Reactions of pyranylidenemethylpyrylium salts with ammonia and amines

Pyranylidenemethylpyrylium salts (1) react with ammonia to give pyranylidenepyridines as a result of the replacement of one of the oxygen atoms of 1 by nitrogen. Aliphatic primary amines react with 1 by replacing both of the oxygen atoms by nitrogens. Aniline and 1 give the monoreplacement product. Pyranylidenemethylthiopyrylium salts have only the oxygen atom replaced by reaction with primary aliphatic amines.     

Reactions of aminophenols with formaldehyde and hydrogen sulfide

The reaction of m-aminophenol with CH₂O and H₂S (1: 2: 1 ratio) afforded 2, 12-dioxa-4, 14-dithia-6, 16-diazatricyclo[15.3.1.1^7,11]docosa-1(20), 7(22), 8, 10, 17(21), 18-hexaene in ∼9% yield. Aminophenol o-and p-isomers react with CH₂O and H₂S (1: 3: 2) to form 2-and 4-[4H-1,3,5-dithiazin-5(6H)-yl]phenols in 86 and 71% yields, respectively. In the crystal structure of the latter, molecules contain dithiazine cycles in the chair conformation with the axial hydroxyphenyl group. Molecular packing represents a combination of molecules forming chains due to the OH...S intermolecular hydrogen bond. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 305–308, February, 2006.     

Reactions of o-bromoacetylacylphenones with several primary amines

o-Monobromoacetylacylphenones, 3a and 3b reacted with hydroxylamine or hydrazine hydrate to produce heterocycles, 2,3-benzoxazine or phthalazine derivatives. The reaction of bromoacetyl group of 3a and 3b with several thioamides afforded thiazole derivatives in high yields. Whereas o-dibromoacetyl-benzophenoe 2a reacted with aniline or cyclohexylamine to produce non-heterocycles, 2-substituted-iminophenylindanones and the mechanism for the formation of these non-heterocycles is proposed.