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Formation of 1,1,2,3,3-pentakis(arylthio)-1-propenes from tris(arylthio)cyclopropenyl cations and their conversion into 1,1,2,5,6,6-hexakis(arylthio)-(3E)-1,3,5-hexatriene

✍ Scribed by Noboru Matsumura; Yasuyo Shimizu; Yoshio Yagyu; Hiroo Inoue; Kazuhiko Mizuno; Tomohiro Adachi

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 257 KB
Volume: 9
Category: Article
ISSN: 1042-7163
DOI: 10.1002/(sici)1098-1071(1998)9:4<387::aid-hc7>3.0.co;2-5

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✦ Synopsis

The reaction of tetrachlorocyclopropene

(1) with arenethiols (2a-e), followed by treatment with perchloric acid, gave tris(arylthio)cyclopropenylium perchlorates (3a-c and e), 1,1,2,3,3-pentakis(arylthio)-1-propenes (4a-d), and 2,3,3tris(arylthio)propenals (5a-d). The structures of tris(phenylthio)cyclopropenylium perchlorate (3a), 1,1,2,3,3-pentakis(phenylthio)-1-propene (4a), and 2,3,3-tris(o-tolylthio)propenal (5b) were analyzed by single-crystal X-ray diffraction studies. The yields depended significantly on the electron-withdrawing property of the substituents of the arenethiols and the molar ratio of 2 to 1. The reaction with 2,6-dimethylbenzenethiol (2e) gave only tris (2,6-dimethylphenylthio)cyclopropenylium perchlorate (3e) without the formation of 4e and 5e. Compounds 5a-d were produced by acid hydrolysis of 4a-d. Pyrolysis of 4a-d gave (3R,4S)-1, 1,2,3,4,5,6,6-octakis(arylthio)-1,5hexadienes (9a-d) and 1,1,2,5,6,6-hexakis(arylthio)-(3E)-1,3,5-hexatrienes (10a-d) together with diaryl di-Dedicated to Prof. Heinrich No ¨th on the occasion of his seventieth birthday.

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