Formation of olefins via pyrolysis of sulfonate esters

…, RF Atkinson, AK Wingard, DJ Halloran…

Index: Corey, E. J.; Posner, Gary H.; Atkinson, Richard F.; Wingard, Astrid K.; Halloran, Daniel J.; et al. Journal of Organic Chemistry, 1989 , vol. 54, # 2 p. 389 - 393

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Citation Number: 41

Abstract

Esters of 8-quinolinesulfonic acid and 2-pyridinesulfonic acid were synthesized from alcohols and the acid chlorides. The secondary esters decomposed cleanly at moderate temperatures to give olefins in high yield. Product studies were consistent with carbocation formation and abstraction by a ring nitrogen to give olefin. The importance of a basic group was confirmed by pyrolysis of a series of para-substituted cyclohexyl benzenesulfonates, ...