Discovery of Deep-Seated Skeletal Rearrangements in the Photocyclizations of Some tert-Butyl-Substituted 1,2-Diarylethylenes

被引：11

作者：

Mallory, Frank B. ^{[1
]}

Regan, Colleen K. ^{[1
]}

Bohen, Joseph M. ^{[1
]}

Mallory, Clelia W. ^{[1
,2
]}

Bohen, Alyssa A. ^{[1
]}

Carroll, Patrick J. ^{[2
]}

机构：

[1] Bryn Mawr Coll, Dept Chem, Bryn Mawr, PA 19010 USA

[2] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 01期

基金：

美国国家科学基金会;

关键词：

STILBENE-LIKE PHOTOCYCLIZATIONS; GRAPHITE RIBBONS; PHOTOCHEMISTRY; PHENACENES; FAMILY; PHENANTHRENES;

D O I：

10.1021/jo501965y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The in-solution oxidative photocyclization of stilbenes to phenanthrenes is a well-known and synthetically valuable reaction. We report here our discovery that the oxidative photocyclization of several tert-butyl-substituted 1-styrylphenanthrenes resulted not only in the expected formation of tert-butyl-substituted picenes but also in the previously unknown rearrangement leading to the formation of tert-butyl-substituted pentahelicenes.

引用

页码：8 / 17

页数：10

共 2 条

[1] Explorations of the solubilizing effectiveness of CH3OCH2CH2O substituents in the photocyclizations of some 1,2-diarylethylenes to [n]phenacenes
Bohen, Alyssa A.
Mullane, Kimberly C.
Bohen, Joseph M.
Mallory, Clelia W.
Mallory, Frank B.
TETRAHEDRON LETTERS, 2015, 56 (23) : 3342 - 3345
[2] IMIDAZO[1,2-B]PYRIDAZINES .13. SYNTHESES AND CENTRAL-NERVOUS-SYSTEM ACTIVITIES OF SOME 2-BENZYL(PHENETHYL, BIPHENYL-4'-YL, 6'-METHYLNAPHTHALEN-2'-YL, TERT-BUTYL AND CYCLOHEXYL)-3-METHOXY(ACYLAMINOMETHYL AND DIMETHYLAMINOMETHYL)-6-(VARIOUSLY SUBSTITUTED)IMIDAZO[1,2-B]PYRIDAZINES
BARLIN, GB
DAVIES, LP
IRELAND, SJ
ZHANG, JK
AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (08) : 1281 - 1300

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