Journal of the American Chemical Society

Photochemical [3+ 2] cycloaddition reactions of alkynones. Diverse fates of two similar vinylcarbene intermediates and reactions of a cyclopropenol

S Wolff, WC Agosta

Index: Wolff,S.; Agosta,W.C. Journal of the American Chemical Society, 1984 , vol. 106, p. 2363

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Citation Number: 15

Abstract

Abstract: Irradiation of alkynone 4 with tetramethylethylene (2) in wet benzene furnishes in high yield the simple cyclopropenol lla. Thermolysis of lla gives the conjugated allenic ketone 5 with loss of C3H6; treatment of lla with sodium hydride leads to 19, and on standing in inert solvent at room temperature lla ejects acetone. In contrast the related alkynone 7 adds 2 photochemically to yield 25, which rearranges at 75 'C to 8. In explanation of the ...