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The thermal deazetations of fluorinated 2,3-diazabicyclo[3.2.0]hept-2-enes

โœ Scribed by William R. Dolbier Jr.; Dheya M. Al-Fekri

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
429 KB
Volume
43
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

Thermal deasetation of difluoro-and tetrafluoro-2,3-diasabicyclo[3.2.0lhept-2-enes proceed via two parallel mechanistic pathways, one involving formation of a diradical via simple N2 loss, and the other proceeding via a retro-dipolar cycloadd~on process. A key finding was the absence of isolation of a bicyclopentane product in the difluoro case.

The thermal deasetation of 2,3-diasabicyclo[3.2.Olhept-2-ene has been shown to take place largely via a retro-1,3dipolar cycloaddition process followed by N2 loss and subsequent rearrange-

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The diazabicyclo[2.2. n] alkenes e, n = l-4) have received considerable attention both for their spectral properties1 and for their thermal nitrogen extrusion reactions. 2 We now report the synthesis of the lowest, and presumably most strained, member of this series, 2,3-diazabicyclo-[2.2.O]hex-2-e