A Facile Synthesis of Difluoromethylene Compounds by Oxidative Fluorodesulfurization of Dithioacetals Using Tetrabutylammonium Dihydrogentrifluoride and N-Halo Compounds

Manabu Kuroboshi; Tamejiro Hiyama

doi:10.1055/s-1991-20920

Synlett 1991; 1991(12): 909-910
DOI: 10.1055/s-1991-20920

letter

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

A Facile Synthesis of Difluoromethylene Compounds by Oxidative Fluorodesulfurization of Dithioacetals Using Tetrabutylammonium Dihydrogentrifluoride and N-Halo Compounds

Manabu Kuroboshi^* , Tamejiro Hiyama

^*Sagami Chemical Research Center, Nishiohnuma 4-4-1, Sagamihara, Kanagawa 229, Japan

Abstract

als PDF herunterladen Alle Artikel dieser Rubrik

Cyclic dithioacetals of aldehydes and ketones are converted into the corresponding difluoromethylene compounds with characteristic chemoselectivity by means of tetrabutylammonium dihydrogen trifluoride and N-halo amides or imides (N-bromosuccinimide, N-iodosuccinimide and 1,3-dibromo-5,5-dimethylhydantoin) in good to excellent yield. The substrates which have an acid-sensitive functionality or other easily fluorinated functionalities give the desired products without any damage to that functionality.

PDF (122 kb)