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

页码：890 / 893

页数：4

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