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Citation: ZHAO Hui, HOU Dong-Yan, YU Hai-Feng, LIU Qun. Thioacetalization Reaction of 1-(1,3-Dithian-2-ylidene)propan-2-one as 1,3-Propandithiol Equivalent[J]. Chinese Journal of Applied Chemistry, ;2009, 26(6): 667-670. shu

Thioacetalization Reaction of 1-(1,3-Dithian-2-ylidene)propan-2-one as 1,3-Propandithiol Equivalent

ZHAO Hui ^a ,
HOU Dong-Yan ^a ,
YU Hai-Feng ^a,b,, ,
LIU Qun ^b

1.
a Department of Chemistry, Anshan Normal College, Anshan 114007;
2.
b Faculty of Chemistry, Northeast Normal University, Changchun 130024

Corresponding author: YU Hai-Feng,
Received Date: 5 June 2008
Available Online: 10 September 2008
Fund Project: 国家自然科学基金(20572013) (20572013)鞍山市科委2007年基金资助项目(2007SF23) (2007SF23)

1-(1,3-Dithian-2-ylidene)propan-2-one(1f),an odorless and stable white crystal at room tempe-rature,was prepared readily in a yield of 86% via decarbonylation of 3-(1,3-dithian-2-ylidene)-pentane-2,4-dione(1b) under acidic condition.Thioacetalization reactions of the odorless 1f as an efficient 1,3-propandithiol equivalent with selected aldehydes and ketones were carried out at room temperature or under reflux in the presence of MeCOCl in MeOH,and 1,3-dithiane derivatives were obtained in high yields(86%~99%).Compared with reported 2-[2-chloro-1-(1-chlorovinyl)allylidene]-1,3-dithiane(1a),3-(1,3)-dithian-2-ylidenepentane-2,4-dione(1b),methyl 2-(1,3-dithian-2-ylidene)-3-oxobutanoate(1c),2-(1,3)dithian-2-ylidene-3-oxo-butanamide(1d) and 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid(1e),compound 1f has better activity as 1,3-propandithiol equivalent in thioacetalization reaction.
- (dithian-ylidene)propan-one,
- thiol equivalents,
- thioacetalization reaction
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