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Benzyne-induced fragmentation of 1,3-oxathiolanes. A novel method for deprotection of carbonyl groups, preparation of phenyl vinyl sulfides, and 1,2-carbonyl transposition

✍ Scribed by Juzo Nakayama; Hidetoshi Sugiura; Atsuko Shiotsuki; Masamatsu Hoshino

Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 278 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)98960-3

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✦ Synopsis

A variety of 1,3-oxathiolanes undergo a benzyne-induced fragmentation leading to phenyl vinyl sulfides and carbonyl compounds. The reaction developed here provides a novel method for deprotection of carbonyl compounds from 1,3-oxathiolanes, preparation of phenyl vinyl sulfides, and 1,2-carbonyl transposition.

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A Novel Method for Protection and Deprot

A Novel Method for Protection and Deprotection of the Carbonyl Groups in 1,2-Indanedione by Conversion to Dioxa-Dithiapropellanes.

✍ Joseph Almog; Yirmi Zehavy; Shmuel Cohen 📂 Article 📅 2003 🏛 John Wiley and Sons ⚖ 82 KB 👁 2 views

## Abstract For Abstract see ChemInform Abstract in Full Text.

A novel method for protection and deprot

A novel method for protection and deprotection of the carbonyl groups in 1,2-indanedione by conversion to dioxa-dithiapropellanes

✍ Joseph Almog; Yirmi Zehavy; Shmuel Cohen 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 171 KB

1,2-Indanedione reacts with two equivalents of 2-mercaptoethanol to produce, instead of the expected 1,2-bis(1,3oxathiolane), a dioxa-dithia[4.4.3] propellane. Other 1,2-indanediones produce analogous compounds. The protecting groups are removed at room temperature with NBS in aqueous acetone, to pr