Journal of the American Chemical Society p. 2837 - 2839 (1982)
Update date:2022-08-04
Topics:
Duncan, James A.
Bohle, D. Scott
Blanchard, Charles A.
Bosse, Mark L.
Noland, Terry W.
et al.
A mixture of syn- and anti-7-(1,2-butadienyl)bicyclo<2.2.1>hept-2-ene <1a (30percent) and 1b (70percent)> has been synthesized through a Grignard reaction employing syn-7-bromonorbornene and 3-bromo-1-butyne.Gas-phase pyrolysis of the mixture at 275 deg C for 24 h gives 1-ethylindan (7) as the single isolable product in 28percent yield.This result is interpreted in terms of an initial concerted <?2s + ?2s + (?2s + ?2a)> rearrangement of 1a to 1-ethylidene-3a,4,5,7a-tetrahydroindene (5), which through a series of not less than five allowed <1,5> hydrogen shifts may give 1-ethylindan.
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