Preparation of Enantiopure trans‐1,2‐Cyclohexanediol and trans‐2‐Aminocyclohexanol

Trans‐1,2‐cyclohexanediol and trans‐2‐aminocycloxexanol are useful chiral auxiliaries. Simple chemical resolution procedures for these molecules are presented.     

Influence of Comonomer Functional Groups on the Reactivity Ratios of Some Phenolic Monomers

The reactivity ratios of some halogen-substituted phenolic monomers have been determined by the linear graphical method of Kelen and Tüdöls. The nature of functional groups present in the comonomer influence the order of reactivity of p-chlorophenol, p-bromophenol, and p-iodophenol. The behavior of these monomers during copolymerization reaction has been interpreted in terms of 1) different degrees of resonance stabilization of the monomers, and 2) opposite polarization caused by the substituents present in the comonomer.     

Note High Yield Synthesis of Low Molecular Weight Poly(Vinyl Acetate) in Aqueous Acidic Media

Polymerization of vinyl acetate continues to interest workers in the field as evidenced by recent publications [1–3]. However, little information is available concerning the synthesis of low molecular weight poly(vinyl acetate) (PVAc) despite its industrial importance.     

A validated HPLC‐PDA method for identification and quantification of two bioactive alkaloids,ephedrine and cryptolepine,in different Sida species

A simple, rapid, accurate and reproducible reverse‐phase HPLC method has been developed for the identification and quantification of two alkaloids ephedrine and cryptolepine in different extracts of Sida species using photodiode array detection. Baseline separation of the two alkaloids was achieved on a Waters RP‐18 X‐terra column (250 × 4.6 mm, 5 µm) using a solvent system consisting of a mixture of water containing 0.1% Trifluoroacetic acid (TFA) and acetonitrile in a gradient elution mode with detection at 210 and 280 nm for ephedrine and cryptolepine, respectively. The calibration curves were linear in a concentration range of 10–250 µg/mL for both the alkaloids with correlation coefficient values >0.99. The limits of detection and quantification for ephedrine and cryptolepine were 5 and 10 µg/mL and 2.5 and 5 µg/mL, respectively. Relative standard deviation values for intra‐day and inter‐day precision were 1.22 and 1.04% for ephedrine and 1.71 and 2.06% for cryptolepine, respectively. Analytical recovery ranged from 92.46 to 103.95%. The developed HPLC method was applied to identify and quantify ephedrine and cryptolepine in different extracts of Sida species. Copyright © 2013 John Wiley & Sons, Ltd.     

Clickable polyurethanes based on s‐triazine ring containing aromatic diisocyanate bearing pendent alkyne group: Synthesis and postmodification

A new s‐triazine ring containing aromatic diisocyanate bearing a pendent alkyne group, namely, 2,4‐bis(4‐isocyanatophenoxy)?6‐(prop‐2‐yn‐1‐yloxy)?1,3,5‐triazine was synthesized and reacted with various diols viz., 1,10‐decanediol, tetraethylene glycol and polyethylene glycols in the presence of dibutyltin dilaurate as the catalyst to obtain a series of linear polyurethanes. The selected polyurethanes possessing pendent alkyne groups were postmodified with chemically diverse azides viz., 1‐(azidomethyl)benzene, 1‐(azidomethyl)pyrene, and methoxy end‐caped poly(ethylene glycol) azide via copper‐catalysed azide‐alkyne Huisgen 1,3‐dipolar cycloaddition. FTIR and ¹H NMR spectra indicated quantitative click reaction. UV–vis and fluorescence spectroscopic analysis confirmed complete incorporation of pyrenyl groups indicating the formation of fluorescence active polyurethane by postmodification with 1‐(azidomethyl)pyrene. TG analysis of polyurethanes indicated two stage weight loss and their thermal stability, as judged by T ₁₀ values, was governed by weight percent of urethane linkages. The water contact angle measurements revealed improved wettability with increased content of PEG either in the backbone of polyurethanes or as grafted chains. DLS and TEM studies confirmed that certain polyurethanes possessing PEG segments displayed self‐assembly in aqueous solution, which was further supported by pyrene encapsulation studies using UV–vis spectroscopy. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017 , 55 , 1008–1020     

Use of allylzinc halide as a source of halide: Differential addition of nucleophiles to Ts-aziridines and aldehydes under similar reaction conditions

We have observed that the allylic zinc halide under identical reaction conditions acts in different modes for different electrophiles. For Ts-aziridines the halide part of the allylic halide has been introduced as a nucleophile and for the carbonyl compounds the simple allylation reaction occurs. To the best of our knowledge this is the first report where the allylic zinc halide is the source of halide acting as nucleophile. The main advantages of the present procedure are easy to handle, no need of inert atmosphere, mild reaction conditions, and applicability to a wide variety of substrates for aziridines and carbonyl compounds.     

A Facile and Convenient Method for the Synthesis of 8-Methoxy 10,11-Dihydronaphtho [1,2-b]Quinolines

Dihydronaphthoquinolines are relatively rare polycyclic heterocyclic compounds. We wish to report a simple and convenient preparative method for hitherto unknown compounds with these new structural features. 6-methoxy tetralone¹ (I) 3.5g (.02 mole) in 3 ml DMF was added slowly to 4.6g (.02 mole) of POCl₃ in 3ml DMF at 0°C. The mixture was stirred for 5 hrs. and the temp. was then gradually raised from 0° to 60–65°C. The resultant complex was treated with aq. sodium acetate solution till pH5–6 was reached. The extract on usual purification, furnished 3.2g (80°%.) of 1-chloro, 6-methoxy, 1,2,3,4 tetrahydro naphthalene-2-aldehyde(II)⁺²