Thallium(I) 1-Propanethiolate

n-PrSTl

[58587-01-2]  · C3H7STl  · Thallium(I) 1-Propanethiolate  · (MW 279.55)

(nucleophile; reagent for preparation of thiol esters)

Solubility: sol in organic solvents.

Form Supplied in: can be readily prepared in situ. Drying: can be dried under vacuum.

Preparative Methods: can be readily prepared starting from 1-propanethiol and thallium(I) ethoxide.1

Handling, Storage, and Precautions: the compound should be stored in a dark bottle under argon. All thallium compounds are extremely toxic to inhalation, skin contact, and ingestion. Toxicity is cumulative. Extreme caution should be used when handling these materials. Use in a fume hood.

General Discussion.

Thallium-1-propanethiolate is a convenient nucleophile for the preparation of thiol esters (see also Thallium(I) 2-Methyl-2-propanethiolate).2 The thiol esters can be prepared starting from diethyl phosphates and thallium 1-propanethiolate (eqs 1-3).3 The reaction conditions are simple, proceed in good yields, and the workup procedure is straightforward.

As indicated in the case of t-BuSTl, the preparation of thiol esters from diethyl phosphates and thallium 1-propanethiolate is the most efficient. Reactions with sodium and potassium thiolates in place of thallium can give unsatisfactory results. The superiority of thallium 1-propanethiolate can be attributed to the ease of preparation and solubility in aprotic solvents.

Thallium 1-propanethiolate can also be used for the formation of metal-sulfur bonds.1,4 An example of this type of transformation in the formation of molybdenum-sulfur bond is shown in eq 4.


1. Carlton, L.; Davidson, J. L. JCS(D) 1987, 895.
2. For alternative methods of thiol ester synthesis, see: Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1991; p 263.
3. Masamune, S.; Kamata, S.; Diakur, J.; Sugihara, Y.; Bates, G. S. CJC 1975, 53, 3693.
4. Davidson, J. L.; Sence, F. JOM 1991, 409, 219.

Mukund P. Sibi

North Dakota State University Fargo, ND, USA

Nancy E. Carpenter

University of Minnesota, Morris, MN, USA



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