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Odorless and Practical Thioacetalization Reagent: Methyl 2-(1,3-Dithian-2-ylidene)-3-oxobutanoate

✍ Scribed by Sun Ran; Liu Qun; Yu Hai-Feng; Zhao Yu-Long; Liu Jun; Ouyang Yan; Dong De-Wen

Publisher: John Wiley and Sons
Year: 2005
Tongue: English
Weight: 62 KB
Volume: 23
Category: Article
ISSN: 0256-7660
DOI: 10.1002/cjoc.200591060

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✦ Synopsis

Abstract

α‐Oxo ketene dithioacetals, methyl 2‐(1,3‐dithian/dithiolan‐2‐ylidene)‐3‐oxobutanoate (2a/2b) prepared in nearly quantitative yields simply from methyl acetylacetate, carbon disulfide and 1,3‐dibromopropane/1,2‐dibro‐ moethane in the presence of potassium carbonate, were investigated in the thioacetalization with various carbonyl compounds 3. It has been demonstrated that methyl 2‐(1,3‐dithian‐2‐ylidene)‐3‐oxobutanoate (2a) could act as a nonthiolic, odorless and practical thioacetalization reagent. A range of aldehydes and ketones 3 were converted into the corresponding dithioacetals 4 in high yields (up to 91%) in the presence of 2a. Moreover, 2a showed high chemoselectivity between aldehyde and ketone in thioacetalization.

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