CYCLOPROPANATION REACTION OF 3-ACYL-2H-1-BENZOPYRAN-2-ONES WITH PHENACYLBROMIDE IN PHASE-TRANSFER SYSTEMS

CYCLOPROPANATION REACTION OF 3-ACYL-2H-1-BENZOPYRAN-2-ONES WITH PHENACYLBROMIDE IN PHASE-TRANSFER SYSTEMS
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DOI:
10.1016/s0040-4020(01)80371-9
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发表时间:
1993-03-12
期刊:
影响因子:
2.1
通讯作者:
RODIOS, NA
RODIOS, NA
中科院分区:
化学3区
文献类型:
--
作者:
BOJILOVA, A;TRENDAFILOVA, A;RODIOS, NA

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3-酰基- 2h -1-苯并吡喃-2-酮1在碱的存在下与苯酰溴反应,以中等产率生成环丙烷衍生物2和3。在相转移条件下,使用Aliquat 336或TPBP催化剂可显著提高反应产物的产率。对这些反应的立体选择性给出了机械的解释。还给出了化合物2和3的光谱数据。
3-Acyl-2H-1-benzopyran-2-ones 1 reacted with phenacylbromide in the presence of a base to give the cyclopropane derivatives 2 and 3 in moderate yields. The yields of the reaction products were substantially improved by using a catalyst (Aliquat 336 or TPBP) under phase-transfer conditions. A mechanistic explanation is given for the stereoselectivity of these reactions. Spectroscopic data for compounds 2 and 3 are also given.