The Journal of Organic Chemistry

Synthesis of methylcubane and cyclopropylcubane. The cubane-1, 4-diyl route

PE Eaton, J Li, SP Upadhyaya

Index: Eaton, Philip E.; Li, Jianchang; Upadhyaya, Subhash P. Journal of Organic Chemistry, 1995 , vol. 60, # 4 p. 966 - 968

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Citation Number: 17

Abstract

6 7 was formed in about 30% yield, and there was less than 5% each of methylcubane and cubane. The bicubyls, important compounds in their own right, are formed from intermediate cubyllithiums adding to cubane-1, 4-diyl (Scheme l). lo This bypath could be suppressed by adding methyl iodide to the reaction. When excess methyllithium was added to a suspension of 1, 4-diiodocubane in ether containing 10 equiv of methyl iodide, the reaction was much ...