Please use this identifier to cite or link to this item: https://scholarbank.nus.edu.sg/handle/10635/75695
Title: Carboxy(vinyl)ketene intermediates in the thermolysis of methylthio- and methoxy-substituted Meldrum's acid derivatives
Authors: Bibas, H.
Kappe, C.O.
Wong, M.W. 
Wentrup, C.
Issue Date: Mar-1998
Citation: Bibas, H.,Kappe, C.O.,Wong, M.W.,Wentrup, C. (1998-03). Carboxy(vinyl)ketene intermediates in the thermolysis of methylthio- and methoxy-substituted Meldrum's acid derivatives. Journal of the Chemical Society. Perkin Transactions 2 (3) : 493-498. ScholarBank@NUS Repository.
Abstract: Methylthio- and methoxy-substituted carboxy(vinyl)ketenes 10 and 16a have been identified by Ar matrix isolation FTIR spectroscopy following flash vacuum thermolysis (FVT) of Meldrum's acid derivatives 7 and 13a. Methylthio(methyl)methyleneketene 9 and alkoxy(methyl)methyleneketene 15 are formed concurrently at high FVT temperatures. The alkoxy(methyl)methyleneketenes 15 do not isomerise to alkoxy(vinyl)ketenes 18, which have been generated and identified in other reactions. Ethoxy(methyl)-methyleneketene 15b readily eliminates ethene in a retro-ene type reaction to produce acetylketene 22. Ketenes 15 react with alcohols and amines to produce 3-alkoxybutenoic acid derivatives 21.
Source Title: Journal of the Chemical Society. Perkin Transactions 2
URI: http://scholarbank.nus.edu.sg/handle/10635/75695
ISSN: 03009580
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