22266-33-7Relevant academic research and scientific papers
Synthesis and Thermal Rearrangement of 7-(1,2-Butadienyl)bicyclohept-2-ene
Duncan, James A.,Bohle, D. Scott,Blanchard, Charles A.,Bosse, Mark L.,Noland, Terry W.,et al.
, p. 2837 - 2839 (1982)
A mixture of syn- and anti-7-(1,2-butadienyl)bicyclohept-2-ene 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 hydrogen shifts may give 1-ethylindan.
