Role of neighboring group participation in the acetolysis of. alpha.-(phenylthio)-. omega.-[(p-tolylsulfonyl) oxy] alkanes

…, A Saba, A Angius, D Casarini

Index: Rosnati, Vittorio; Saba, Antonio; Angius, Antonella; Casarini, Daniele Journal of Organic Chemistry, 1987 , vol. 52, # 18 p. 4094 - 4098

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Abstract

In order to evaluate the relative importance of the neighboring group participation by the phenylthio group, the acetolysis of tosylates la-e has been studied. The results obtained confirmed that the participation decreases with the increasing ring size of the intermediate cyclic sulfonium salts 2 in the order S-3> S-5> S-6. Among these salts only 2c and 2d were isolated, while the formation of 2b and 2e was indirectly demonstrated by the obtainment ...