36367-84-7Relevant academic research and scientific papers
Photoreactions of Halogenobenzenes with Cyclopentene. Insertion into Carbon-Halogen Bonds
Bryce-Smith, Derek,Dadson, W. Mike,Gilbert, Andrew
, p. 112 - 113 (1980)
Chloro-, bromo-, and iodo-benzenes photoreact with cyclopentene to give, principally, products derived from insertion into the C-halogen bond, a type of reaction hitherto unknown in this series, but fluorobenzene mainly forms meta- and para-cycloadducts w
Elimination Promoted by Weak Bases. IX. Stereochemistry of Olefin Formation from trans-2-Phenylcyclopentyl p-Bromobenzenesulfonate Promoted by Lithium Chloride in Acetone
McLennan, Duncan J.,Lim, Gaik-Choo
, p. 1821 - 1830 (2007/10/02)
Parker, Winstein, and their coworkers have previously established that in the E2C elimination of trans-2-phenylcyclopentyl p-bromobenzenesulfonate induced by Bu4NCl in acetone some 9percent of the olefinic product is produced by a syn-elimination.In view of the current idea that syn-eliminations in solution are assisted by association of the base with its counterion, the stereochemistry of the reaction induced by lithium chloride in acetone has been studied.There is no increase in the amount of syn-elimination, and kinetic analysis reveals that lithium chloride ion pairs are completely unreactive. 1-Phenylcyclopentene is not produced by rate-limiting attack of chloride on a preformed symmetrical phenonium ion pair.These results do not serve to distinguish between two alternative models of the E2C transition state.
