Title: Reactions of 4-chlorothiopyrylium cation with nucleophiles
Abstract: Reactions of 4-chlorothiopyrylium cation (1) with a variety of nucleophiles have been investigated. Thiophenol, aniline, N-methylaniline, sodium phenoxide and sodium methoxide reacted with 1 to give 4-substituted products. On the other hand, Grignard reagents and alkyl amines afforded ring-opened products by nucleophilic attack at the 2-position. The difference in reaction position according to the kind of nucleophile can be reasonably intrepreted in terms of the principle of hard and soft acids and bases. The “aromatic character” of thiopyrylium cation is discussed on the basis of the relative reactivities in nucleophilic substitution of 1, N-methyl-4-chloropyridinium (2) and 4-chloropyrylium (8) cations.
Publication Year: 1975
Publication Date: 1975-01-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 11
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