Synthesis of 2'-Alkylspiro [2-X-cyclohexan-1, 3'-3'H-indole](X= H; X= CH3) by an Unexpected Reaction between an Organomagnesium Halide and 2'-Methylspiro [2-X- …

…, M Paz Martínez-Alcazar, I Fonseca

Index: Rodriguez, J. Gonzalo; Urrutia, Anahi; De Diego, J. Eugenio; Martinez-Alcazar, M. Paz; Fonseca Journal of Organic Chemistry, 1998 , vol. 63, # 13 p. 4332 - 4337

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Citation Number: 9

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 ...