Formation of Olefins via Pyrolysis of Sulfonate Esters

Article abstract of DOI:10.1021/jo00263a024

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 hight 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, p-XC6H4SO3R.The compounds with X=NHEt and NHCOMe reacted cleanly to give olefin in good yield.When X = NO2, Br, CH3, or OCH3, olefin was formed in low yield along with considerable amounts of tar.