The cleavage reaction of some 1, 3-benzoxathioles with magnesium bromide and acetic anhydride has been studied. In all the 1, 3-benzoxathioles studied, the opening of the heterocyclic ring occurs first with cleavage of the C [BOND] O bond and formation of bromides and their corresponding products of hydrolysis. Successively also the cleavage of the C [BOND] S bond can occur. The competitive electrophilic substitution on the benzene ring becomes appreciable only in the 1, 3-benzoxathioles-2, 2-disubstituted with sterically demanding groups.
Studies on the synthesis of heterocyclic compounds. XIV. Cleavage of 1,3‐benzoxathioles by magnesium bromide‐acetic anhydride
FADDA, ANNA MARIA;MACCIONI, ANNA MARIA;
1984-01-01
Abstract
The cleavage reaction of some 1, 3-benzoxathioles with magnesium bromide and acetic anhydride has been studied. In all the 1, 3-benzoxathioles studied, the opening of the heterocyclic ring occurs first with cleavage of the C [BOND] O bond and formation of bromides and their corresponding products of hydrolysis. Successively also the cleavage of the C [BOND] S bond can occur. The competitive electrophilic substitution on the benzene ring becomes appreciable only in the 1, 3-benzoxathioles-2, 2-disubstituted with sterically demanding groups.
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