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

Ran Sun | Zendy; Qun Liu | Zendy; HaiFeng Yu | Zendy; YuLong Zhao | Zendy; Jun Liu | Zendy; Yan Ouyang | Zendy; DeWen Dong | Zendy

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

Author(s) -

Ran Sun,

Qun Liu,

HaiFeng Yu,

YuLong Zhao,

Jun Liu,

Yan Ouyang,

DeWen Dong

Publication year - 2005

Publication title -

chinese journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.28

H-Index - 41

eISSN - 1614-7065

pISSN - 1001-604X

DOI - 10.1002/cjoc.200591060

Subject(s) - chemistry , chemoselectivity , reagent , carbon disulfide , aldehyde , ketone , ketene , potassium carbonate , carbanion , organic chemistry , medicinal chemistry , catalysis

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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