Cycloaddition reactions of trimethylenemethane radical cation generated from methylenecyclopropanone thioacetal

被引：38

作者：

Nakamura, M ^{[1
]}

Toganoh, M ^{[1
]}

Ohara, H ^{[1
]}

Nakamura, E ^{[1
]}

机构：

[1] Univ Tokyo, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 01期

关键词：

D O I：

10.1021/ol9900055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new trimethylenemethane precursor, methylenecyclopropanone thioacetal 2, was synthesized, Trimethylenemethane species generated from 2 showed broad reactivities toward electron-deficient and electron-rich olefins under thermal or photochemical conditions.

引用

页码：7 / 9

页数：3

共 11 条

[1] PREPARATION AND DISPROPORTIONATIVE-HYDROLYSIS OF CYCLOPROPANONE THIOACETALS - NEW METHOD OF HOMOLOGATION [J].

BRAUN, M ;

SEEBACH, D .

CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (02) :669-691

[2] REGIOSELECTIVE AND ENDO-STEREOSELECTIVE [3 + 2] CYCLOADDITION OF DIPOLAR TRIMETHYLENEMETHANE TO ELECTRON-DEFICIENT OLEFIN [J].

EJIRI, S ;

YAMAGO, S ;

NAKAMURA, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (22) :8707-8708

[3] Direct observation of two different types of TMM intermediates in the photoinduced electron-transfer degenerate methylenecyclopropane rearrangement [J].

Ikeda, H ;

Nakamura, T ;

Miyashi, T ;

Goodman, JL ;

Akiyama, K ;

Tero-Kubota, S ;

Houmam, A ;

Wayner, DDM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (23) :5832-5833

[4] SYNTHESIS AND [2+2] CYCLOADDITION OF DIMETHYLENEKETENE ACETALS - REACTION WITH C-60 AND FACILE HYDROLYSIS OF THE C-C BOND CONNECTED TO C-60 [J].

YAMAGO, S ;

TAKEICHI, A ;

NAKAMURA, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) :1123-1124

[5] IN-VIVO BIOLOGICAL BEHAVIOR OF A WATER-MISCIBLE FULLERENE - C-14 LABELING, ABSORPTION, DISTRIBUTION, EXCRETION AND ACUTE TOXICITY [J].

YAMAGO, S ;

TOKUYAMA, H ;

NAKAMURA, E ;

KIKUCHI, K ;

KANANISHI, S ;

SUEKI, K ;

NAKAHARA, H ;

ENOMOTO, S ;

AMBE, F .

CHEMISTRY & BIOLOGY, 1995, 2 (06) :385-389

[6] USE OF METHYLENECYCLOPROPANONE KETALS FOR CYCLOPENTANE SYNTHESIS - A NEW EFFICIENT THERMAL [3 + 2] CYCLO-ADDITION [J].

YAMAGO, S ;

NAKAMURA, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (18) :7285-7286

[7] THERMAL HETERO[3+2]CYCLOADDITION APPROACH TO FUNCTIONALIZED TETRAHYDROFURANS [J].

YAMAGO, S ;

NAKAMURA, E .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) :5553-5555

[8] Thermal hetero[3+2] cycloaddition of dipolar trimethylenemethane to O-alkyloximes.: Straightforward synthetic routes to substituted pyrrolidines and prolines [J].

Yamago, S ;

Nakamura, M ;

Wang, XQ ;

Yanagawa, M ;

Tokumitsu, S ;

Nakamura, E .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05) :1694-1703

[9] A CONCISE SYNTHETIC ROUTE TO CYCLOPENTENES BY [3+2]-CYCLOADDITION OF DIPOLAR TRIMETHYLENEMETHANE TO ALKYNES [J].

YAMAGO, S ;

EJIRI, S ;

NAKAMURA, E .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (19) :2154-2156

[10] SINGLE-ELECTRON TRANSFER PATHWAY IN THE [3+2] CYCLOADDITION OF DIPOLAR TRIMETHYLENEMETHANE WITH OLEFINS [J].

YAMAGO, S ;

EJIRI, S ;

NAKAMURA, M ;

NAKAMURA, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5344-5345

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