Sulfo fluorenylmethoxycarbonyl Chloride

Wittig-type Reaction. TsNSO undergoes an interesting Wlttlg-type reaction with triphenylphosphonlum fluorenylide to afford thione 5-imides in good yields (eq 14).  

For uses of related iVsulfinyl compounds such as i 7sulfii l (6 (trimethylsilyl)ethyl)sulfonamide and A7sulfinyl-(p-methylphei l) methanesulfonamide see Garigipati, R. S. Tschaen, D. M. Weinreb, 

Kresze, G. In 1,4 Cycloaddition Reactions, the Diels-AlderReaction in HeteixxycUc Synthesis, Hamer, J., Ed. Academic New York, 1967 p 453. 

The thermal Diels Alder reaction of Ai-alkyl-Ai-sulfinyl dienophileswith l,3 11enes fails except in the presence of a Lewis acid catalyst or under high pressure. See Bell, S. I. Weinreb, S. M., Tetrahedron Lett. 1988, 29, 4233. 

This A7sullinyl compound was prepared from benzyl carbamate with thloi l chloride and pyridine. Garigipati, R. S. Freyer, A. J. Whltde, R. R. Weinreb, S. M., J. Am. Chem. Soc. 1984, 106, 7861. 

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