MIGRATION RATIOS IN THE REARRANGEMENT OF 2-AMINO-1,1-DIARYLETHANOLS
MIGRATION RATIOS IN THE REARRANGEMENT OF 2-AMINO-1,1-DIARYLETHANOLS
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DOI：
10.1021/ja01643a037
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发表时间：
1954-01-01
影响因子：
15
通讯作者：
CREW, MC
中科院分区：
文献类型：
--
作者：
CURTIN, DY;CREW, MC
2-氨基-1-对-茴香基-1-苯基乙醇和2-氨基-1-苯基-1-对-甲苯基乙醇的重排，以前报道的只产生分别由对-茴香基或对-甲苯基迁移形成的产物，已经被重新检查，并且发现对-茴香基/苯基的迁移比仅为1.5，而对-甲苯基/苯基的迁移比为1.3，与以前的报道相反。类似氨基醇的重排导致对-氯苯基/苯基的迁移比为0.9，对-茴香基/对-甲苯基的迁移比为1.2。2-氨基-对-茴香基-1-苯基乙醇（I）与亚硝酸的重排已被报道导致<$-甲氧基苄基苯基酮（由对-茴香基迁移形成），而没有分离出另一种异构体，对-茴香基苄基酮。3相应的β-乙氧基苯基氨基醇得到了类似的结果，尽管在这种情况下，除了据报道形成的β-乙氧基苄基苯基酮之外，还可以分离出少量的β-乙氧基苯基苄基酮。另一组分析师4检测了2-氨基-1-苯基-1-对甲苯基乙醇（II）的重排，并报告了对甲基苄基苯基酮（由对甲苯基迁移形成）是分离的唯一产物。结合其他工作，希望更准确地了解这类氨基醇重排中的迁移率。
The rearrangements of 2-amino-1-^-anisyl-1-phenylethanol and 2-amino-l-phenyl-l-^-tolylethanol, previously reported to yield only the product formed with migration of the£-anisyl or p-tolyl group, respectively, have been re-examined and the migration ratio of^-anisyl/phenyl has been found to be only 1.5 while that of¿-tolyl/phenyl is 1.3 contrary to the previous reports. Rearrangement of similar amino alcoholsleads to the migration ratios for^-chlorophenyl/phenyl of 0.9 and for p-anisyl//>-tolyl of 1.2.The rearrangement of 2-amino-lp-anisyl-l-phen-ylethanol (I) with nitrous acid has been reported to lead to¿>-methoxybenzyl phenyl ketone (formed by migration of the p-anisyl group) and none of the other isomer,^-anisyl benzyl ketone was isolated. 3 The corresponding£>-ethoxyphenyl amino alcohol gave similar results although in this case a small amount ofp-ethoxyphenyl benzyl ketone could be isolated in addition to the^-ethoxybenzyl phenyl ketone which was reported to be formed in much larger quantity. A differentgroup of investigat-ors4 examined the rearrangement of 2-amino-lphenyl-lp-tolylethanol (II) and reported p-methylbenzyl phenyl ketone (formed with£-tolyl migration) to be the sole product isolated. In connection with other work, it was desired to know more exactly the migration ratios in the rear-rangement of amino alcohols of this type.