1, 2, 4-Dithiazolidine-3, 5-dione as an isocyanate equivalent in the Mitsunobu reaction

ME Wood, DJ Cane-Honeysett…

Index: Wood, Mark E.; Cane-Honeysett, Daniel J.; Dowle, Michael D. Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 18 p. 2046 - 2047

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Abstract

The remarkably high acidity of 1,2,4-dithiazolidine-3,5-dione 1 (pK a = 2.85) 3 suggested that it should be a synthetically useful nucleophile in this procedure (Fig. 1). Most importantly, N-alkylated derivatives 2 can be readily transformed into either amines 4 or isocyanates 3 (by very mild thiolysis or treatment with triphenylphosphine under anhydrous conditions respectively), whilst being stable towards commonly encountered acidic, mildly basic and photolytic deprotection ...