著者

di FURIA F.

雑誌

Synthesis

巻号頁・発行日

vol.1984,

被引用文献数

3 296

著者

Oh Ken Fuchibe Kohei Yokota Misaki Ichikawa Junji

出版者

Georg Thieme Verlag

雑誌

Synthesis (ISSN:00397881)

巻号頁・発行日

vol.2012, no.6, pp.857-861, 2012-03

被引用文献数

16

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Two methods for the difluorovinylidenation of carbonyl compounds have been developed to synthesize 1,1-difluoroallenes bearing various substituents. The reaction of 1-bromo-2,2-difluorovinyllithium, generated from 1,1-dibromo-2,2-difluoroethylene and n-butyllithium, with aldehydes or ketones, and subsequent acetylation, gives 2-bromo-3,3-difluoroallylic acetates. Elimination of these acetates with n-butyllithium affords 1,1-difluoroallenes in high yield. 3,3-Difluoro-2-iodoallylic acetates are similarly prepared from aldehydes or ketones on treatment with 2,2-difluoro-1-iodovinyllithium, generated from 1,1,1-trifluoro-2-iodoethane and lithium diisopropylamide, followed by acetylation. These acetates readily undergo elimination with zinc metal to afford 1,1-difluoroallenes in high yield.

著者

Oh Ken Fuchibe Kohei Ichikawa Junji

出版者

Georg Thieme Verlag

雑誌

Synthesis (ISSN:00397881)

巻号頁・発行日

vol.2011, no.6, pp.881-886, 2011-03

被引用文献数

2 5

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1,1-Difluoroallenes are synthesized in good yield via zinc-promoted 1,2-elimination of 3,3-difluoro-2-iodoallylic acetates, which are prepared by the reaction of aldehydes or ketones with 1-iodo-2,2-difluorovinyllithium, generated from commercially available 1,1,1-trifluoro-2-iodoethane.Key words