Please use this identifier to cite or link to this item:
https://scholarbank.nus.edu.sg/handle/10635/94678
DC Field | Value | |
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dc.title | Reactions of diastereomeric 2,4,5-triphenyl-1,3-dioxolans with N-bromosuccinimide and t-butyl perbenzoate | |
dc.contributor.author | Lee, H.-H. | |
dc.contributor.author | Chen, S.-F. | |
dc.date.accessioned | 2014-10-16T08:38:50Z | |
dc.date.available | 2014-10-16T08:38:50Z | |
dc.date.issued | 1978 | |
dc.identifier.citation | 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. | |
dc.identifier.issn | 14727781 | |
dc.identifier.uri | http://scholarbank.nus.edu.sg/handle/10635/94678 | |
dc.description.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. | |
dc.source | Scopus | |
dc.type | Article | |
dc.contributor.department | CHEMISTRY | |
dc.description.sourcetitle | Journal of the Chemical Society, Perkin Transactions 1 | |
dc.description.issue | 3 | |
dc.description.page | 270-274 | |
dc.identifier.isiut | NOT_IN_WOS | |
Appears in Collections: | Staff Publications |
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