Premium
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.