Generation and Rearrangement of (1-Hydroxycyclopropyl)- and (1-Hydroxycyclobutyl)carbene

被引：3
|
作者：
DeAngelo, Joseph D. [1 ]
Hatano, Sayaka [2 ]
Thamattoor, Dasan M. [1 ]
机构：
[1] Colby Coll, Dept Chem, Waterville, ME 04901 USA
[2] Hiroshima Univ, Dept Chem, Grad Sch Sci, 1-3-1 Kagamiyama, Hiroshima 7398526, Japan
来源：
AUSTRALIAN JOURNAL OF CHEMISTRY | 2019年 / 72卷 / 11期
基金：
美国国家科学基金会;
关键词：
RING-EXPANSION; CARBENE;
D O I：
10.1071/CH19379
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Photolysis of exo-1-(1a,9b-dihydro-1H-cyclopropa[l]phenanthren-1-yl)cyclopropan-1-ol and exo-1-(1a,9b-dihydro-1H-cyclopropa[l]phenanthren-1-yl)cyclobutan-1-ol in benzene-d6 produces (1-hydroxycyclopropyl)- and (1-hydroxycyclobutyl)carbene respectively. It was observed that (1-hydroxycyclopropyl)carbene rearranges to cyclobutanone whereas (1-hydroxycyclobutyl)carbene forms cyclopentanone. Formation of both ketones is attributed to tautomerization of the corresponding enols that arise from ring expansion of the carbenes. Products assignable to intramolecular C-H insertions were not detected in the photolysates.
引用
收藏
页码：890 / 893
页数：4
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