The Journal of Organic Chemistry

Synthesis of 2-benzylidenebenzocyclobutenones via an intramolecular Stille coupling reaction

JC Bradley, T Durst

Index: Bradley, J. C.; Durst, T. Journal of Organic Chemistry, 1991 , vol. 56, # 18 p. 5459 - 5462

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Citation Number: 20

Abstract

Compounds 2a and 3a were obtained as orange and bright yellow solids, respectively. Each showed strong absorption at 1766 cm-'and a single vinylic hydrogen at 6 6.62 and 6.29, respectively. The specific stereochemical assignment is based on NOE studies. Thus, irradiation of the vinylic peak of 2 (6 6.62) gave an NOE response only in the ortho hydrogens of the phenyl group. In contrast, irradiation of the 6 6.29 peak in 3 gave an ...