Abstract
Abstract The simplest examples of both a five-membered cyclic sulfonic anhydride (ethane-1, 2-disulfonic anhydride, 3) and a sulfonylammonium salt (2, 2-dimethylisothiazolidinium 1, 1-dioxide fluorosulfate, 13), are found to react with triethylamine and an alcohol via direct displacement at sulfur and not by way of the sulfene. When taken with previous observations these results lead to the conclusion that five-membered cyclic sulfonic acid derivatives can generally be expected to react entirely by direct displacement, even in those reactions in which the acylic or six-membered cyclic analogues react entirely via the sulfene.
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