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

PD Bartlett, AAM Roof, R Subramanyam…

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

Full Text: HTML

Citation Number: 14

Abstract

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 ...