Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/94678
Title: Reactions of diastereomeric 2,4,5-triphenyl-1,3-dioxolans with N-bromosuccinimide and t-butyl perbenzoate
Authors: Lee, H.-H. 
Chen, S.-F.
Issue Date: 1978
Source: Lee, H.-H.,Chen, S.-F. (1978). Reactions of diastereomeric 2,4,5-triphenyl-1,3-dioxolans with N-bromosuccinimide and t-butyl perbenzoate. Journal of the Chemical Society, Perkin Transactions 1 (3) : 270-274. ScholarBank@NUS Repository.
Abstract: Two diastereomeric 2,4,5-triphenyl-1,3-dioxolans isolated from the acetalization of meso-hydrobenzoin with benzaldehyde have been assigned their respective configurations based on spectroscopic evidence. The reactions of r-2,c-4,t-5-triphenyl-1,3-dioxolan (4) with N-bromosuccinimide and with t-butyl perbenzoate catalysed by cuprous chloride have been shown to give erythro-1-benzoyloxy-2-bromo-1,2-diphenylethane and meso-hydrobenzoin dibenzoate respectively. The corresponding reactions of r-2,c-,.c-5-triphenyl-1,3-dioxolan (5) and r-2, t-4, t-5-triphenyl-1,3-dioxolan (6), on the other hand, gave threo-1-benzoyloxy-2-bromo-1,2-diphenylethane and (±)-hydrobenzoin dibenzoate respectively. These stereospecific results are consistent with SN2 ring opening involving a dioxolenyl cation.
Source Title: Journal of the Chemical Society, Perkin Transactions 1
URI: http://scholarbank.nus.edu.sg/handle/10635/94678
ISSN: 14727781
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