PERHALO KETONES .V. REACTION OF PERHALOACETONES WITH AROMATIC HYDROCARBONS

PERHALO KETONES .V. REACTION OF PERHALOACETONES WITH AROMATIC HYDROCARBONS
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DOI:
10.1021/jo01015a009
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发表时间:
1965-01-01
影响因子:
3.6
通讯作者:
SIBILIA, JP
SIBILIA, JP
中科院分区:
化学2区
文献类型:
--
作者:
FARAH, BS;GILBERT, EE;SIBILIA, JP

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过卤丙酮(X3CCOCX3, X= F, Cl)与各种芳烃及其卤化和烷基化衍生物缩合,可制得28种一般结构为RCCCXskOH的新甲醇。使用氯化铝作为催化剂,产率随着酮中氯含量的增加而降低。这些新化合物在化学上和热上都很稳定。对其中六种化合物的核磁共振研究表明,由于相邻的2-羟基六氟-2-丙基的吸电子作用,相邻的芳香或甲基质子产生了去屏蔽效应。
Condensation of perhaloacetones (X3CCOCX3, X= F, Cl), with various aromatic hydrocarbons, and with their halogenated and alkylated derivatives, has led tothe preparation of 28 new carbinols of the general structure RCCCXskOH. Using aluminum chloride as catalyst, yields decreased as the ketone used contained progressively more chlorine. The new compounds are chemically and thermally stable. An nmr study of six of the compounds showed deshielding effects in adjacent aromatic or methyl protons resulting from the electronwithdrawing effect of an adjacent 2-hydroxyhexafluoro-2-propyl group.