Unusual Reactions of Magnesium Indolates with Benzenesulfonyl Chloride
Grignard reagents from N-unsubstituted indoles and benzenesulfonyl chloride undergo reaction such as to produce unstable intermediates of β-chlorination and a-sulfonylation, which are transformed into oxindoles or substituted indoles. In the same reaction, yuehchukene (the naturally occurring dehydroprenylindole dimer) is converted into a spirooxindole, containing a strained four-membered ring, which is changed into a spirooxindole isomer with ring expansion on mild acid treatment. © 1987, American Chemical Society. All rights reserved.
Wenkert, E; Moeller, PDR; Piettre, SR; McPhail, AT
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