Addition reactions to syn-and anti-sesquinorbornenes involving ionic mechanisms: the role of tetracyanoethylene

PD Bartlett, AAM Roof, R Subramanyam…

文献索引：Bartlett, Paul D.; Roof, Antonius A. M.; Subramanyam, Ravi; Winter, William J. Journal of Organic Chemistry, 1984 , vol. 49, # 11 p. 1875 - 1880

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被引用次数: 14

摘要

Addition of bromine or of acids to anti-sesquinorbornene is more rapid and less readily reversible than that to the syn isomer, whereas other addition reactions proceeding by concerted or free-radical mechanisms show a small rate advantage for syn- sesquinorbornene and no reversibility. Tetracyanoethylene (TCNE) does not undergo cycloaddition with syn-or anti-sesquinorbomene, nor can any dipolar ion from TCNE and ...