STEREOSELECTIVITY OF OXIDATION OF 2-SUBSTITUTED-1,3-DITHIOLANES
Authors:
- 1 June 1981
- journal article
- research article
- Published by Taylor & Francis in Phosphorus and Sulfur and the Related Elements
- Vol. 10 (2) , 163-168
Abstract
The stereoselectivity of oxidation of 2-methyl-1,3-dithiolane (3), 2-phenyl-1,3-dithiolane (7), and 2-tert-butyl-1,3-dithiolane (15) with sodium metaperiodate and with m-chloroperoxybenzoic acid affords primarily the trans-1-oxide corresponding to attack from the less-hindered side. The trans/cis ratio varies from 3/2 for oxidation of 3 to cleanly trans for 15. Further oxidation of 1,3-dithiolane 1-oxides produces trans-1,3-dioxides. The 13C NMR spectra of the oxidation products provide valuable clues for stereochemical determination.Keywords
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