Use of phenyl vinyl sulfoxide as an acetylene equivalent in Diels-Alder cycloadditions

LA Paquette, RE Moerck, B Harirchian…

文献索引：Paquette,L.A. et al. Journal of the American Chemical Society, 1978 , vol. 100, # 5 p. 1597 - 1599

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被引用次数: 101

摘要

Structural assignment to 3 as the syn, cis [2+ 21 cyclopentadiene dimer follows from its spectral properties: IH NMR (C6D6) 6 2.25 (m, 4 H), 2.89 (m, 2 H), 3.42 (m, 2 H), 5.44 (m, 2 H), and 5.77-5.83 (br m, 2 H). Double resonance studies revealed that independent saturation of the 6 2.89 and 5.44 signals causes the downfield olefinic peak to become a doublet (J= 5.1 Hz) and triplet (J= 4.0 Hz), respectively. Mechanistically instructive is the ...