PHOTOISOMERIZATION OF ACYCLIC CONJUGATED CYCLOPROPYL CARBONYL COMPOUNDS

被引:26
作者
DAUBEN, WG
SHAFFER, GW
机构
[1] University of California, Berkeley
[2] Givaudan Corporation, Clifton
关键词
D O I
10.1021/jo01260a013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The photochemistry of the acyclic vinylcyclopropane carbonyl chromophore has been studied. Using Corex-filtered light, dihydrofurans (4-6), δ,εunsaturated acids (7 and 8), and epoxycyclobutanes (9 and 10) were found. The mechanism for the formation of these materials are discussed, and all reactions involve conjugative opening of the cyclopropane ring (eq 6 and 7). The formation of a ketene from an acyclic aldehyde is a new process and it has been shown to proceed intramolecularly (eq 8). © 1969, American Chemical Society. All rights reserved.
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页码:2301 / &
相关论文
共 18 条
[1]   PHOTOLYSIS OF 3-METHYLCAR-4-EN-2-ONE [J].
BELLAMY, AJ ;
WHITHAM, GH .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (OCT) :4035-&
[2]   THE CHEMISTRY OF THE TRITERPENES AND RELATED COMPOUNDS .18. ELUCIDATION OF THE STRUCTURE OF POLYPORENIC ACID-C [J].
BOWERS, A ;
HALSALL, TG ;
JONES, ERH ;
LEMIN, AJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1953, (SEP) :2548-2560
[3]   METHYLSULFINYL CARBANION (CH3-SO-CH2-) . FORMATION AND APPLICATIONS TO ORGANIC SYNTHESIS [J].
COREY, EJ ;
CHAYKOVSKY, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1345-+
[4]   SOLUTION PHOTOLYSIS OF CIS- AND TRANS-2-METHYLCYCLOPROPYL METHYL KETONE [J].
DAUBEN, WG ;
SCHUTTE, L ;
WOLF, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (06) :1849-&
[5]  
DAUBEN WG, 1967, TETRAHEDRON LETT, P4415
[6]   THERMAL ISOMERIZATION OF 1-CYCLOPROPYL-2-METHYLPROPENE [J].
ELLIOTT, CS ;
FREY, HM .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (JAN) :345-&
[7]  
FLOWERS MC, 1961, J CHEM SOC, P3547
[8]   STRUCTURE AND REACTIVITY IN VAPOR-PHASE PHOTOLYSIS OF KETONES .V. ALIPHATIC CYCLOPROPYL AND OLEFINIC KETONES [J].
HESS, LD ;
JACOBSON, JL ;
SCHAFFNE.K ;
PITTS, JN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (15) :3684-&
[9]  
JACKMAN LM, 1964, APPLICATIONS NMR SPE, P62
[10]  
JULIA M, 1959, CR HEBD ACAD SCI, V248, P242