Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/94380
Title: Novel formation of 4-methylthiopyrene in a hofmann elimination reaction directed toward the synthesis of 17,19-dioxa[2.2.3](1,2,3)cyclophanediene
Authors: Lai, Y.-H. 
Eu, H.-L.
Issue Date: 1993
Source: Lai, Y.-H.,Eu, H.-L. (1993). Novel formation of 4-methylthiopyrene in a hofmann elimination reaction directed toward the synthesis of 17,19-dioxa[2.2.3](1,2,3)cyclophanediene. Journal of the Chemical Society, Perkin Transactions 1 (2) : 233-237. ScholarBank@NUS Repository.
Abstract: The synthesis of 17,19-dioxa[2.2.3](1,2,3)cyclophanediene was attempted via a Stevens rearrangement-Hofmann elimination sequence on 19,21-dioxa-2,11- dithia[3.3.3](1,2,3)cyclophane. Pyrene and 4-methylthiopyrene were, however, the isolated products. The structure of the latter was fully characterized by UV, MS, 1D and 2D 1H NMR spectra. Formation of 4-methylthiopyrene was expected to involve a novel base-induced ring cyclization resulting in elimination of methanoate an ion from the methylenedioxy bridge followed by a novel 1,4-hydride shift resulting in the elimination of methane.
Source Title: Journal of the Chemical Society, Perkin Transactions 1
URI: http://scholarbank.nus.edu.sg/handle/10635/94380
ISSN: 14727781
Appears in Collections:Staff Publications

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