Thermally induced cyclobutenone rearrangements and domino reactions

被引：36

作者：

Harrowven, David C. ^{[1
]}

Pascoe, David D. ^{[1
]}

Guy, Ian L. ^{[1
]}

机构：

[1] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 03期

基金：

英国工程与自然科学研究理事会;

关键词：

cyclization; domino reactions; rearrangement; spiro compounds; thermochemistry;

D O I：

10.1002/anie.200603538

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Four thermal-rearrangement pathways and a domino reaction leading to quinones arise from the thermolysis of cyclobutenones. The course of vinylcyclobutenone rearrangements is dictated by the nature of the substituent, R (see scheme): a cyclopentenone arises when R is an electron-rich alkene. In other cases thermolysis gives a cyclohexadienone, which may collapse with elimination to form a quinone, or tautomerize into a hydroquinone or cyclohexenedione. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：425 / 428

页数：4

共 31 条

[11] New metathesis methodology leading to angularly-fused polycyclic quinones and related compounds [J].

Heileman, MJ ;

Tiedemann, R ;

Moore, HW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3801-3802

[12]

Hoffmann H. M. R., 1969, ANGEW CHEM, V81, P597, DOI DOI 10.1002/ANGE.19690811603

[13] ENE REACTION [J].

HOFFMANN, HM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (08) :556-&

[14] tert-butyl substituent as a regiodirecting and novel C-H protecting group in cyclobutenedione-based benzannulation chemistry [J].

Liu, FQ ;

Liebeskind, LS .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2835-2844

[15] ASYMMETRIC ENE REACTIONS IN ORGANIC-SYNTHESIS [J].

MIKAMI, K ;

SHIMIZU, M .

CHEMICAL REVIEWS, 1992, 92 (05) :1021-1050

[16] GENERAL REGIOSPECIFIC SYNTHESIS OF ANNULATED QUINONES [J].

MOORE, HW ;

PERRI, ST .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :996-1003

[17]

MOORE HW, 1995, ADV STR ORG, V4, P81

[18] Vinylcyclobutane-cyclohexene rearrangement: Theoretical exploration of mechanism and relationship to the Diels-Alder potential surface [J].

Northrop, BH ;

Houk, KN .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :3-13

[19] A new photoannulation reaction of 2-aryl-3-alkoxy-1,4-naphthquinones. Synthesis of dimethylnaphthgeranine E [J].

Onofrey, TJ ;

Gomez, D ;

Winters, M ;

Moore, HW .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5658-5659

[20] Squaric acid ester-based total synthesis of echinochrome A [J].

Peña-Cabrera, E ;

Liebeskind, LS .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (05) :1689-1691

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