Perhalo Ketones. VII. Phenolic Derivatives of the Perhaloacetones
Perhalo Ketones. VII. Phenolic Derivatives of the Perhaloacetones
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Perhalo 酮。
DOI：
10.1021/jo01015a011
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发表时间：
1965
期刊：
影响因子：
--
通讯作者：
J. Sibilia
中科院分区：
文献类型：
--
作者：
B. Farah;E. Gilbert;M. Litt;J. A. Otto;J. Sibilia
本文报道了由二氯丙酮、五氟一氯丙酮和六氟丙酮与各种一元酚、二元酚和酚醚缩合合成的三十种新甲醇。采用几种酸性催化剂，其选择决定了进入的2-羟基全卤代-2-丙基的取向是酚基的邻位还是帕拉。对其中九种化合物的核磁共振研究表明，给电子的羟基和烷基在很大程度上中和了进入的高度氟化烷基的吸电子作用。本研究是作为六氟丙酮和类似物的反应和衍生物的一般计划的一部分进行的。全卤代氟氯酮。[2]关于三种酚类化合物与其中两种酮反应的简要报道已经出现。3.4 Knunyants和同事3表明，苯酚与六氟丙酮以2：1的摩尔比在100下在大量无水HF存在下反应10小时，形成“双酚”。
Thirty new carbinols have been prepared by condensation of tetrafluorodichloro-, pentafluoromonochloro-, and hexafluoroacetones with various mono- and dihydric phenols and with phenolic ethers. Several acidic catalysts were employed, the choice of which determines whether orientation of the entering 2-hydroxyperhalo-2-propyl group is ortho or para to the phenolic group. An nmr study of nine of the compounds indicated that electron-donating hydroxyl and alkyl groups largely neutralize the electron-withdrawing effectof the entering highly fluorinated alkyl group.The present study was undertaken as part of a general program on reactions and derivatives of hexafluoro-acetone and the analogous perhalogenatedfluorochloro ketones. 2 Brief reports on the reaction of three phenolic compounds with two of these ketones have already appeared. 3· 4 Knunyants and co-workers3 showed that phenol reacts with hexafluoroacetone at 2: 1 molar ratio at 100 for 10 hr. in the presence of a large quantity of anhydrous HF to form a “bisphenol”