Tetrahedron letters

A novel method for protection and deprotection of the carbonyl groups in 1, 2-indanedione by conversion to dioxa-dithiapropellanes

J Almog, Y Zehavy, S Cohen

Index: Almog, Joseph; Zehavy, Yirmi; Cohen, Shmuel Tetrahedron Letters, 2003 , vol. 44, # 16 p. 3285 - 3288

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Citation Number: 8

Abstract

1, 2-Indanedione reacts with two equivalents of 2-mercaptoethanol to produce, instead of the expected 1, 2-bis (1, 3-oxathiolane), a dioxa-dithia [4.4. 3] propellane. Other 1, 2- indanediones produce analogous compounds. The protecting groups are removed at room temperature with NBS in aqueous acetone, to produce the original diketone.