Synthetic applications of 2-chloro-1,3-dithiane preparation of ketene dithioacetals

✍ Scribed by C.G. Kruse; N.L.J.M. Broekhof; A. Wijsman; A. Van der gen

• Publisher: Elsevier Science
• Year: 1977
• Tongue: French
• Weight: 249 KB
• Volume: 18
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)92782-0

✦ Synopsis

Since their original conception by Corey and Seebaah, P-lithio-l,j_dithianea have found widespread application in organic synthesis as masked carbonyl oompounds with a nuoleophilio central carbon atom. 2 Considerable broadening of the synthetic scope of 1,4_dithianes might be expeoted if this carbon atom could also be converted into an eleotrophilic oentre. Beoently, the first successful chlorination of l,>dithiene with N-chloroeuooinimide was reported by Arai and Oki.

Although the resulting P-chloro-l,+dithiane was not isolated in a pure state, its identity was clearly shown by nmr studies and by its reaations with nucleophiles.

In this communication we report a simple, high yield synthesis of 2-chloro-1,3-dithisne which allows its isolation as a crystalline solid, and the oonversion of this oompound into a number of useful synthetic intermediates, in particular phoephorue ylids.