Journal of Organic Chemistry p. 2159 - 2162 (1988)
Update date:2022-08-11
Topics:
Abelt, Christopher J.
Pleier, Jennifer M.
Phenylmethyldiazirine forms a stable, solid complex with β-cyclodextrin.The diazirine was decomposed by pyrolysis or irradiation of the complex, and the reaction products were analyzed.The major volatile products consist of the isomeric 1,2-diphenyl-1-methylcyclopropanes.Under photolytic conditions a significant amount of styrene also is formed.The selectivity for trans isomer formation is 10 times greater from the CD complex than from the neat state.Carbene insertion products with β-cyclodextrin are formed under both reaction conditions.The product distributions are explained by cage and shape-selective effects exerted by β-cyclodextrin.
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