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Application of carbene reactive intermediates in organic synthesis: III. Reaction of difluorocarbene with trimethylsilyl enol ethers
Author(s) -
Wu ShiHui,
Yu Qing
Publication year - 1989
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19890070310
Subject(s) - difluorocarbene , chemistry , carbene , enol , nitroethane , organic chemistry , trimethylsilyl , enol ether , acetophenone , cyclohexanone , cyclopentene , medicinal chemistry , catalysis
The addition of difluorocarbene generated from phenyl(trifluoromethyl)mercury and anhydrous sodium iodide, with trimethylsilyl enol ethers derived from cyclohexanone, cycloheptanone, 3‐pentanone and acetophenone was described. The corresponding 2, 2‐difluoro‐1‐trimethylsilyloxy‐cyclopropanes were obtained in good yields. The thermal stability of these cyclopropyl derivatives was affected by the molecular strain and the nature of their substituents. Thus, 1‐trimethylsilyloxy‐cyclopentene reacted with difluorocarbene to give only 2‐fluoro‐2‐cyclohexen‐1‐one instead of the expected 1‐trimethylsilyloxy‐6, 6‐difluorobicyclo [3.1.0]hexane, and a mechanism for its formation was proposed.