𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Reactions of cyclic sulfur ylides with some carbonyl compounds

✍ Scribed by Hitoshi Akiyama; Katsuyoshi Ohshima; Tetsuya Fujimoto; Iwao Yamamoto; Ryozo Iriye

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
161 KB
Volume
13
Category
Article
ISSN
1042-7163

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The reaction of a six‐membered sulfonium ylide 5 with aldehydes or ketones afforded the oxirane derivatives 6a–d as a mixture of cis and trans isomers in excellent yields. In addition, the same reactions, using five‐ or six‐membered cyclic oxosulfonium ylides 7 and 11, gave the corresponding oxirane derivatives in good yields. Moreover, the reaction of 11 with two equimolar amounts of base and 4‐hexen‐3‐one afforded the cyclooctene oxide derivative 16 with high stereoselectivity in 59% yield via a sequential Michael–Michael‐type addition of the ylide and the resulting enolate ion followed by an intramolecular Corey–Chaykovsky reaction. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:216–222, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10022

📜 SIMILAR VOLUMES

The Reaction of Some α-Oxygenated Cyclic
The Reaction of Some α-Oxygenated Cyclic Ketones with Sulfur Ylides
✍ Marschner, Christoph ;Baumgartner, Judith ;Griengl, Herfried 📂 Article 📅 1994 🏛 John Wiley and Sons 🌐 English ⚖ 604 KB

## Abstract Cyclopentanones 1, 4 and 7, as well as uloses 11, 14, 17, and 20, all possessing an oxygen atom in α‐position with respect to the carbonyl group, have been allowed to react with dimethylsulfonium and dimethyloxosulfonium methylides. It has been found that the nucleophilic attack can be

ChemInform Abstract: Reaction of Dimetho
ChemInform Abstract: Reaction of Dimethoxycarbene with Strained Cyclic Carbonyl Compounds.
✍ Paul C. Venneri; John Warkentin 📂 Article 📅 2001 🏛 John Wiley and Sons ⚖ 37 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v