Archiv der Pharmazie p. 977 - 983 (1993)
Update date:2022-08-04
Topics:
Rettberg
Wagner
Hartke
Aliphatic dithiocarboxylic acids such as dithioethanoic acid (1a), dithiopropanoic acid (10a) or 2-methyl-dithiopropanoic acid (10e) react with 2 moles of n-BuLi to form the corresponding dilithium dithioenolates 2a, 11a or 11e. These add to aldehydes and ketones to give the aldol adducts 3a-f and 12a-e. Methylation with methyl iodide leads to the more stable β-hydroxy dithioesters 4 and 13. The esters 4 have been dehydrated to yield the α,β-unsaturated dithioesters 5. Addition of the dilithium dithioenolate 2a to methylvinyl ketone, cyclohexenone or cyclopentenone followed by methylation gives rise to the δ,ε-unsaturated dithioesters 6-8.
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Doi:10.1039/c3cc46633g
(2014)Doi:10.1021/jo00089a004
(1994)Doi:10.1021/jo00073a002
(1993)Doi:10.1016/0022-328X(94)80106-1
(1994)Doi:10.1039/DT9940002697
(1994)Doi:10.1016/0040-4039(94)85016-X
(1994)