J. Rodríguez, A. Urrutia, J. E. D. Diego
Jun 11, 1998
Citations
0
Influential Citations
11
Citations
Journal
Journal of Organic Chemistry
Abstract
The reaction of 2‘-methylspiro[cyclohexan-1,3‘-3‘H-indole] (1a) with methylmagnesium iodide gives 2‘-ethyl-, 2‘-isopropyl-, and 2‘-tert-butylspiro[cyclohexan-1,3‘-3‘H-indole] as the unexpected 2‘-methyl insertion products; their presence and ratio are dependent upon the reaction conditions. Influence of a methyl substituent in 2‘-methylspiro[2-methylcyclohexan-1,3‘-3‘H-indole] (1b) on the reaction with methylmagnesium iodide has been analyzed; the 2‘-ethyl (2b) and 2‘-isopropyl (3b) derivatives were obtained as the insertion products together with a luminescent compound that was identified by X-ray diffraction analysis as meso-(1R,2S),(1S,2R)-α,β-di{(2‘-(spiro[2-methylcyclohexan-1,3‘-3'H-indolyl]}ethene (10). The reaction of 1a or 1b with some active organomagnesium halides (allyl or benzyl) afforded the 2‘-methyl-2‘-alkyl-3‘H-indole derivative (allyl, 5a or 5b; benzyl, 6a) as an apparent addition product. The reaction possibly occurs through a mechanism of radical intermediates.