Synthesis and structure of aliphatic phenylchloronium ylide

✍ Scribed by Masahito Ochiai; Norihiro Tada; Kazunori Miyamoto; Motoo Shiro

• Book ID: 102233828
• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 171 KB
• Volume: 22
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20683

✦ Synopsis

Abstract

Aliphatic phenylchloronium ylide with bis(trifluoromethylsulfonyl)‐methylidene group was synthesized. Thermal transylidation of 4‐(trifluoromethyl)phenylbromonium bis(trifluoromethylsulfonyl)methylide in chlorobenzene as a solvent at 130°C afforded phenylchloronium bis(trifluoromethylsulfonyl)methylide in a moderate yield. Phenylbromonium and phenyliodonium ylides were also prepared by the thermal transylidation to bromo‐ and iodobenzenes. The reaction probably involves initial thermal generation of bissulfonylcarbene (Tf~2~C:), followed by nucleophilic attack of a halobenzene toward the electron‐deficient carbene center. Solid‐state structures of these aliphatic phenylhalonium ylides were analyzed and compared with each other. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:325–330, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20683