Benzyne, cyclohexyne, and 3-azacyclohexyne and the problem of cycloalkyne versus cycloalkylideneketene genesis

C Wentrup, R Blanch, H Briehl…

Index: Wentrup,C.; Blanch,R.; Briehl,H. Journal of the American Chemical Society, 1988 , vol. 110, p. 1874

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Citation Number: 132

Abstract

Abstract: Benzyne, cyclohexyne, and 3-azacyclohexyne have been obtained by flash vacuum pyrolysis of phthalic anhydride, 4-cyclopentylidene-3-methylisoxazol-5 (4H)-one (34), and 3-methyl-4-(2-pyrrolidinylidene) isoxazol-5 (4H)-one (37), respectively, isolated at 77 K and observed by IR spectroscopy. Trapping and fragmentation reactions are described, and the implications for the mechanism of benzyne formation from phthalic anhydride via ...