Unusual Behavior of the Anionic Species from (E)-1-Chloro-3,3,3-trifluoropropene (HCFC-1233t)

✍ Scribed by Akiko Miyagawa; Motoki Naka; Takashi Yamazaki; Tomoko Kawasaki-Takasuka

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 155 KB
• Volume: 2009
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200900370

✦ Synopsis

Abstract

(E)‐1‐Chloro‐3,3,3‐trifluoropropene was smoothly deprotonated by MeLi at the position β to the CF~3~ group, and exclusive formation of propargylic alcohols was observed by addition of appropriate carbonyl compounds as long as up to 1.6 equiv. of MeLi was used, whereas more than 1.7 equiv. of this base led to selective construction of allylic alcohols. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)