ChemInform Abstract: REACTION OF SULFUR, SULFUR MONOCHLORIDE, AND SULFUR DICHLORIDE WITH CARBOXYLIC ACID N-HALOAMIDES

1979 ◽  
Vol 10 (29) ◽  
Author(s):  
G. S. BOROVIKOVA ◽  
E. S. LEVCHENKO ◽  
E. M. DOROKHOVA
Keyword(s):  
Carboxylic Acid ◽  
Sulfur Monochloride ◽  
Sulfur Dichloride

Acetylenic acids. II. The reaction of sulfur chlorides with phenylpropiolic acid and its methyl ester

1978 ◽  
Vol 31 (3) ◽  
pp. 605 ◽  
Author(s):  
WN Lok ◽  
AD Ward
Keyword(s):  
Methyl Ester ◽  
Acid Chloride ◽  
Thionyl Chloride ◽  
Sulfuryl Chloride ◽  
Acid Form ◽  
Sulfur Monochloride ◽  
Sulfur Dichloride ◽  
Acetylenic Acids

The reactions of phenylpropiolic acid and methyl phenylpropiolate with thionyl chloride, sulfur monochloride, sulfur dichloride and sulfuryl chloride have been investigated. With thionyl chloride the presence of pyridine is necessary for a reaction to occur with the ester or for the reaction to proceed beyond the acid chloride stage in the case of the acid. In all cases the Z and E isomers of 2,3-dichlorocinnamic acid or its methyl ester are among the main products that have been identified. With all but sulfuryl chloride a 3-chloro-1-benzothiophen system is also formed. Sulfuryl chloride and phenylpropiolic acid form 4-chloro-1-phenylnaphthalene-2,3-dicarboxylic anhydride in low yield. The structures of other minor products and the pathways leading to all these products are discussed.

Acetylenic Acids. IV. The Reactions of Alkoxy-Substituted Phenylpropiolic Acids and Esters with Sulfur Halides, Particularly Thionyl Chloride

1979 ◽  
Vol 32 (4) ◽  
pp. 833 ◽  
Author(s):  
CM Bonnin ◽  
PA Cadby ◽  
CG Freeman ◽  
AD Ward
Keyword(s):  
Thionyl Chloride ◽  
Major Product ◽  
Sulfur Monochloride ◽  
Sulfur Dichloride ◽  
Substituted 1 ◽  
Acetylenic Acids

3,4-Dialkoxy-substituted phenylpropiolic acids and esters react with thionyl chloride to give good yields of substituted 1-benzothiophen systems. Similar reactions of m-and p-methoxyphenylpropiolic acids and 3,4,5-trimethoxyphenylpropiolic acid, which yield mixtures of products, are reported. In contrast, 2,5- and 2,3-dimethoxyphenylpropiolic acids gave mixtures in which a coumarin is the major product. The effect of adding pyridine to the reaction mixture is outlined. Reactions involving sulfur monochloride and sulfur dichloride generally gave much lower yields of these products. Attempts to form organometallic intermediates from the 3-chloro-1-benzothiophen products were unsuccessful.

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