A general, regioselective approach to the synthesis of ortho allylanilines

Article abstract of DOI:10.1016/00404-0399(50)09297-

Readily available 2,1-benzothiazines can be alkylated via deprotonation with butyllithium followed by treatment with iodomethyltrimethylsilane. Subsequent treatment with fluoride and hydrolysis leads to ortho allyl anilines in high yield. The reaction is general and regioselective by virtue of these characteristics being present in the Lewis acid mediated reaction of alkenes and sulfonimidoyl chlorides, the reaction which leads to the 2,1-benzothiazines used as starting materials.