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Studies on heterocyclic chemistry. part 21. Reaction of 3-mercapto-and 3-acylthio-3-isothiazoline-5-thiones : Ring transfomations, a baseinduced ring cleavage, and thiol-ester-thioxo-ester rearrangements

Journal of the Chemical Society. Perkin transactions 1 : organic and bio-organic chemistry Volume 1980 Page 2693-2699
published_at 1980
Title
Studies on heterocyclic chemistry. part 21. Reaction of 3-mercapto-and 3-acylthio-3-isothiazoline-5-thiones : Ring transfomations, a baseinduced ring cleavage, and thiol-ester-thioxo-ester rearrangements
Creators Nishiwaki Tarozaemon
Creators Kawamura Etsuko
Creators Abe Noritaka
Creators Iori Mitsuo
Acylation of 4-aryl-3-mercapto-3-isothiazoline-5-thiones (1) with acid chloride in pyridine or alternatively with acid anhydride leads exclusively to 3-acylthio-4-aryl-3-isothiazoline-5-thiones (2). Reactions of (1) with reactive acetylenes afford 2-[aryl(thiocarbamoyl)methylene]-1,3-dithiole derivatives (3) whereas those of (2) with the acetylenes are accompanied by an S → N acyl migration giving N-benzoyl-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]arylethanethioamides (4). ^<13>C N.m.r. spectra and some chemical reactions of (3) and (4) are described. The ring-cleavage of (1) with base and the thiol-easter-thioxo-easter rearrangements of (2) induced by diazoalkane, alkyl iodide, or triethyloxonium tetrafluoroborate are also reported.
Languages eng
Resource Type journal article
Publishers Royal Society of Chemistry
Date Issued 1980
File Version Not Applicable (or Unknown)
Access Rights metadata only access
Relations
[ISSN]0300-922X
[NCID]AA00695134
info:doi/10.1039/P19800002693
[isVersionOf] [URI]http://www.rsc.org/Publishing/Journals/P1/
Schools 大学院医学系研究科(理学)