Journal of the American Chemical Society

Discovery of a new fragmentation reaction

PA Wender, CJ Manly

Index: Wender, Paul A.; Manly, Charles J. Journal of the American Chemical Society, 1990 , vol. 112, # 23 p. 8579 - 8581

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Citation Number: 13

Abstract

Qr 1 0 at 25 OC in the presence of diphenylisobenzofuran (DIBF) afforded crystalline adduct 6 in 24% yield after chromatography. The structure of 6 (C, symmetry) was confidently assigned from spectral data and DDQ oxidation to 7.9 Ample literature precedent supports the conclusion that 6 is formed from [2+ 41 cycloaddition of cumulene 1 at its most strained A Synthesis of conjugated enyne 2 (Scheme 11) follows a similar strategy in the final step. ...