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The Journal of Organic Chemistry

Effects of temperature on atom transfer cyclization reactions of allylic. alpha.-iodo esters and amides

DP Curran, J Tamine

文献索引:Curran, Dennis P.; Tamine, John Journal of Organic Chemistry, 1991 , vol. 56, # 8 p. 2746 - 2750

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被引用次数: 196

摘要

Atom-transfer cyclizations of allyl iodoacetatee and N-allyl-N-methyliodoacetamides are much more efficient at 80" C than at 25" C. At 80" C, & (iodomethyl) lactones and lactams are formed rapidly and in good yield under standard atom-transfer conditions (sunlamp irradiation of iodide and 10% hexabutylditin in benzene for 10-60 min). It is proposed that this temperature effect is responsible for some unusual observations by Jolly and ...