Premium
1,3‐benzoxathioles. Electrophilic aromatic substitution
Author(s) -
Cabiddu Salvatore,
Cerioni Giovanni,
Cocco Maria Teresa,
Maccioni Antonio,
Plumitallo Antonio
Publication year - 1982
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570190126
Subject(s) - chemistry , nitration , nitric acid , acetic anhydride , acetic acid , electrophilic aromatic substitution , electrophilic substitution , acylation , electrophile , halogenation , organic chemistry , nitrate , substitution reaction , derivative (finance) , medicinal chemistry , catalysis , financial economics , economics
Some electrophilic substitution reactions on 1,3‐benzoxathiole derivatives are described. Bromination and acylation reactions take place in position 5, i.e., para to the oxygen atom. 1,3‐Benzoxathiole nitration yields a mixture of the corresponding sulfoxide and of the 6‐nitro derivative when performed with 33% nitric acid, while, using a mixture of 40% nitric acid and acetic acid or acetyl nitrate, the 6‐nitroderivative is obtained together with large amounts of gummy products. 2,2‐Dimethyl‐1,3‐benzoxathiole nitration with 33% nitric acid yields disulfide XI, while with 33% nitric acid and acetic acid or with acetyl nitrate a mixture of disulfide XI and XII is obtained. The structure of the products have been determined by spectroscopic methods.