Syntheses and Pyrolyses of Furan Analogues of α-Oxo-o-quinodimethanes. Formation of Methylenecyclobutenone and 1-Buten-3-yne via a Vinylcarbene– …

PW Tseng, CY Kung, HY Chen…

Index: Tseng, Pen-Wen; Kung, Chen-Yu; Chen, Hsing-Yin; Chou, Chin-Hsing Journal of Organic Chemistry, 2011 , vol. 76, # 20 p. 8440 - 8446

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Citation Number: 8

Abstract

Flash vacuum pyrolyses (FVP) of benzoic 2-methyl-3-furoic anhydride (12) and benzoic 3- methyl-2-furoic anhydride (13) at 550° C and ca. 10–2 Torr both give methylenecyclobutenone (16) and 1-buten-3-yne (17) as the main products. A mechanism involving generation of furan analogues of α-oxo-o-quinodimethane, 10 and 11, from FVP of 12 and 13, respectively, followed by elimination of a CO molecule to give the respective ...