CYCLOPENTADIENONE EPOXIDE - SYNTHESIS AND PHOTOCHEMISTRY

被引：36

作者：

CHAPMAN, OL

HESS, TC

机构：

[1] Department of Chemistry, University of California-Los Angeles, Los Angeles

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 06期

关键词：

D O I：

10.1021/jo01320a015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4,5-Epoxy-2-cyclopenten-l-one (2) was prepared by the vacuum pyrolysis of the dimethyl phthalate Diels-Alder adduct (8). Cyclopentadienone epoxide (2) was shown to be reasonably thermally stable but reactive toward nucleophilic and electrophilic reagents. Photolysis of matrix isolated 1 produces α-pyrone (10) and the aldehyde ene ke-tene (9). © 1979, American Chemical Society. All rights reserved.

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页码：962 / 964

页数：3

相关论文

共 21 条

[1] CONFORMATIONAL EQUILIBRIUM TRAPPING BY HIGH-VACUUM CRYOGENIC DEPOSITION [J].

ANET, FAL ;

SQUILLACOTE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (11) :3243-3244

[2] 4-PYRONE PHOTOCHEMISTRY - INTERMEDIACY OF A CYCLOPENTADIENONE EPOXIDE [J].

BARLTROP, JA ;

DAY, AC ;

SAMUEL, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (17) :598-599

[3]

CHAPMAN OL, UNPUBLISHED

[4] LEVULINIC ACID AS A REAGENT FOR THE HYDROLYSIS OF OXIMES AND 2,4-DINITROPHENYLHYDRAZONES [J].

DEPUY, CH ;

PONDER, BW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (17) :4629-4631

[5] DIAZOCYCLOPENTADIENE [J].

DOERING, WV ;

DEPUY, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (23) :5955-5957

[6] PERICYCLIC REACTIONS . SYNTHESIS AND REACTIONS OF DEUTERIUM LABELLED CYCLOHEXA-1,4-DIENE AND CYCLOHEXA-1,3-DIENE [J].

FLEMING, I ;

WILDSMIT.E .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (04) :223-&

[7] PHOTOISOMERIZATION OF 4H-PYRAN-4-ONES TO 2H-PYRAN-2-ONES [J].

ISHIBE, N ;

SUNAMI, M ;

ODANI, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :463-468

[8]

KANE M, UNPUBLISHED

[9]

KWANTES A, 1958, GAS CHROMATOGRAPHY 1

[10]

PADWA A, 1964, TETRAHEDRON LETT, P813