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Synlett 2002(6): 0984-0986
DOI: 10.1055/s-2002-31921
DOI: 10.1055/s-2002-31921
LETTER
© Georg Thieme Verlag Stuttgart · New York
Heteroaromatic Dithioacetals, Part II: Evidence of a Novel Mechanism for the Exclusive Formation of Unsymmetrical Dithioacetals.
Further Information
Received
26 March 2002
Publication Date:
07 February 2007 (online)
Publication History
Publication Date:
07 February 2007 (online)
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Abstract
The exclusive production of unsymmetrical dithioacetals in the BF3·Et2O catalyzed thioacetalization of aldehydes results from novel and unsuspected mechanistic considerations.
Key words
aldehydes - thiols - condensation - Lewis acids - carbonyl complexes
- 1
Gauthier JY.Zajac N.Mayhew DL.Hughes GJ.Martins E.Guay D.Young RN.Zamboni RJ. Synlett 1998, 289 ; and references therein -
3a
Young RN.Gauthier JY.Thérien M.Zamboni RJ. Heterocycles 1989, 967 ; and references therein -
3b
Isidor JL.Carson RM. J. Org. Chem. 1973, 554 - 4
Ravindranathan T.Chavan SP.Tejwani RB.Varghese JP. J. Chem. Soc., Chem. Commun. 1991, 1750
References
To a 0 °C CH3CN solution (15 mL) of 2 (2.8 mmol., 0.994 g), 4-chlorobenzaldehyde (2.9 mmol., 0.411 g) and 4-mercaptopyridine (6 mmol., 0.668 g) was added BF3·OEt2 (9.7 mmol., 1.2 mL) dropwise. The mixture was allowed to warm to 25 °C and stirred for 16 hours. It was worked up and purified as previously described [1] to yield 1 (1.883 g., 96%).