Synthesis and thermal rearrangement of 7-(1, 2-butadien-1-yl) bicyclo [2.2. 1] hept-2-ene [7-(3-methylallenyl) norbornene]

JA Duncan, DS Bohle, CA Blanchard…

Index: Duncan, James A.; Bohle, D. Scott; Blanchard, Charles A.; Bosse, Mark L.; Noland, Terry W.; et al. Journal of the American Chemical Society, 1982 , vol. 104, # 10 p. 2837 - 2839

Full Text: HTML

Citation Number: 2

Abstract

Abstract: A mixture of syn-and anti-7-(1, 2-butadienyl) bicyclo [2.2. l] hept-2-ene [la (30%) and lb (70%)] has been synthesized through a Grignard reaction employing syn-7- bromonorbornene and 3-bromo-1-butyne. Gas-phase pyrolysis of the mixture at 275 OC for 24 h gives 1-ethylindan (7) as the single isolable product in 28% yield. This result is interpreted in terms of an initial concerted [, 2,+. 2,+(, 28+, 2a)] rearrangement of la to l- ...