Synthesis of α,β-unsaturated aldehydes and methyl carboxylic esters from 2-acetylenic phenyl sulfides

Article abstract of DOI:10.1080/00397919708005915

2-Alkynylthio benzenes were reduced to 2-Alkenylthio benzenes with diisobutyl aluminum hydride. Mono chlorination of these compounds with sulfuryl chloride and pyridine followed by hydrolysis, in the presence of Cu(II) salts, gave α,β-unsaturated aldehydes. 2-Alkynylthio benzenes were converted into 2-Alkynyl 1,1-bis thiobenzenes by monochlorination with sulfuryl chloride and pyridine followed by treatment with thiophenol and triethylamine. These substances were then converted to α,β-unsaturated methyl carboxylic esters by way of isomerization with sodium methoxide to the corresponding allene and treatment with hydrochloric acid and methanolysis in the presence of iodine.

Full text of DOI:10.1080/00397919708005915

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Synthetic Communications: An
International Journal for Rapid
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Organic Chemistry
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Synthesis of α,β-Unsaturated
Aldehydes and Methyl
Carboxylic Esters from 2-
Acetylenic Phenyl Sulfides.
Carlos C. Fortes a & Clevia F. D. Garrote a
a Departamento de Quimica , Universidade de
Brasilia , 70919-970 CP, DF, 04478, Brazil
Published online: 22 Aug 2006.
To cite this article: Carlos C. Fortes & Clevia F. D. Garrote (1997) Synthesis
of α,β-Unsaturated Aldehydes and Methyl Carboxylic Esters from 2-Acetylenic
Phenyl Sulfides., Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 27:22, 3917-3941
To link to this article: http://dx.doi.org/10.1080/00397919708005915
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