[14204-27-4]  · C14H9NO2S  · N-Phenylthiophthalimide  · (MW 255.31)

(mild sulfenylating reagent)

Physical Data: mp 160-161 °C; colorless solid.

Preparative Method: by reaction of Benzenesulfenyl Chloride with Phthalimide in the presence of Triethylamine.1

General Discussion.

N-Phenylthiophthalimide has been shown to be a mild sulfenylating reagent that is useful for a range of synthetic applications. This reagent reacts with amines2 and thiols3 to give the corresponding sulfenyl amines and disulfides respectively (eq 1).

Upon reaction with Grignard reagents or organolithium compounds, mixed sulfides are formed (eq 2).4

Activated carbonyl compounds can be cleanly bis-sulfenylated by this reagent in the presence of Et3N (eq 3).5

Bis-sulfenylation of g-butyrolactone, as well as of cyclic ketones, has been achieved with this reagent via the corresponding lithium enolates.6 This reaction has been utilized in an efficient synthesis of 3-substituted 2-buten-4-olides (eq 4).

1. Behforouz, M.; Kerwood, J. E. JOC 1969, 34, 51.
2. Harpp, D. N.; Back, T. G. TL 1971, 12, 4953.
3. Boustany, K. S.; Sullivan, A. B. TL 1970, 11, 3547.
4. Furukawa, M.; Suda, T.; Hayashi, S. S 1974, 282.
5. Grossert, J. S.; Dubey, P. K. CC 1982, 1183.
6. Watanabe, M.; Shirai, K.; Kumamoto, T. NKK 1982, 1780.

Tom Livinghouse

Montana State University, Bozeman, MT, USA

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