Accession Number : AD0710857

Title :   REACTION OF 2,3-DIMETHYLINDOLE WITH 2,4-DINITROPHENYLSULFENYL CHLORIDE: AN UNEXPECTED PRODUCT,

Corporate Author : NATIONAL RESEARCH COUNCIL OF CANADA HALIFAX (NOVA SCOTIA) ATLANTIC REGIONAL LAB

Personal Author(s) : Hutzinger,O. ; Raj,R. K.

Report Date : 23 JAN 1970

Pagination or Media Count : 3

Abstract : Evidence was produced recently that electrophilic substitution in the 2-position of indole occurs in certain cases by attack of the electrophilic reagent at position 3 and subsequent rearrangement. With 2,3-disubstituted indoles the rearrangement should not occur and the 'intermediate' indolenine derivative would be expected as the final product. When 2,4-dinitrophenylsulfenyl chloride (DNPSCl) was allowed to react with 2,3-dimethylindole, and unexpected compound, 3-methylindole-2-methylene-2',4'-dinitrophenyl sulfide, was formed as the major product. (Author)

Descriptors :   (*INDOLES, *SUBSTITUTION REACTIONS), ORGANIC SULFUR COMPOUNDS, NUCLEAR MAGNETIC RESONANCE, ORGANIC NITROGEN COMPOUNDS, NITROBENZENES

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE