STEREOSELECTIVE SYNTHESIS OF BOTH (E)-1,2,4-HEPTATRIEN-6-YNES AND (Z)-1,2,4-HEPTATRIEN-6-YNES - FORMATION OF AN ALPHA,3-DEHYDROTOLUENE BIRADICAL, TRAPPING BY AN INTRAMOLECULAR CARBON CARBON DOUBLE-BOND, AND DECAY OF THE RESULTING NEW BIRADICAL VIA AN INTRAMOLECULAR ROUTE

被引：43

作者：

ANDEMICHAEL, YW ^{[1
]}

GU, YG ^{[1
]}

WANG, KK ^{[1
]}

机构：

[1] W VIRGINIA UNIV,DEPT CHEM,MORGANTOWN,WV 26506

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 03期

关键词：

D O I：

10.1021/jo00029a002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation between conjugated allenic aldehydes 3 and gamma-(trimethylsilyl)allenylboranes 2 followed by the Peterson olefination reaction afforded enyne-alleness 7 and 8. On heating, 8c underwent a sequence of intramolecular transformations through biradical intermediates.

引用

页码：794 / 796

页数：3

共 45 条

[21] CALICHEMICINS, A NOVEL FAMILY OF ANTITUMOR ANTIBIOTICS .1. CHEMISTRY AND PARTIAL STRUCTURE OF CALICHEMICIN-GAMMA-1
LEE, MD
DUNNE, TS
SIEGEL, MM
CHANG, CC
MORTON, GO
BORDERS, DB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) : 3464 - 3466
[22] KINETIC EVIDENCE FOR THE FORMATION OF DISCRETE 1,4-DEHYDROBENZENE INTERMEDIATES - TRAPPING BY INTERMOLECULAR AND INTRAMOLECULAR HYDROGEN-ATOM TRANSFER AND OBSERVATION OF HIGH-TEMPERATURE CIDNP
LOCKHART, TP
COMITA, PB
BERGMAN, RG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (14) : 4082 - 4090
[23] MARCH J, 1985, ADV ORG CHEM, P166
[24] STEREOCHEMICAL ASSIGNMENT OF NEOCARZINOSTATIN CHROMOPHORE - STRUCTURES OF NEOCARZINOSTATIN CHROMOPHORE METHYL THIOGLYCOLATE ADDUCTS
MYERS, AG
PROTEAU, PJ
HANDEL, TM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (21) : 7212 - 7214
[25] DESIGN AND DYNAMICS OF A CHEMICALLY TRIGGERED REACTION CASCADE LEADING TO BIRADICAL FORMATION AT SUBAMBIENT TEMPERATURE
MYERS, AG
DRAGOVICH, PS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (25) : 9130 - 9132
[26] THERMAL GENERATION OF ALPHA,3-DEHYDROTOLUENE FROM (Z)-1,2,4-HEPTATRIEN-6-YNE
MYERS, AG
KUO, EY
FINNEY, NS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) : 8057 - 8059
[27] BIRADICAL FORMATION FROM ACYCLIC CONJUGATED ENEYNE-ALLENE SYSTEM RELATED TO NEOCARZINOSTATIN AND ESPERAMICIN-CALICHEMICIN
NAGATA, R
YAMANAKA, H
OKAZAKI, E
SAITO, I
[J]. TETRAHEDRON LETTERS, 1989, 30 (37) : 4995 - 4998
[28] DNA CLEAVAGE BY ACYCLIC ENEYNE-ALLENE SYSTEMS RELATED TO NEOCARZINOSTATIN AND ESPERAMICIN-CALICHEAMICIN
NAGATA, R
YAMANAKA, H
MURAHASHI, E
SAITO, I
[J]. TETRAHEDRON LETTERS, 1990, 31 (20) : 2907 - 2910
[29] SYNTHESIS AND CHEMISTRY OF DYNEMICIN-A MODELS
NICOLAOU, KC
SMITH, AL
WENDEBORN, SV
HWANG, CK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (08) : 3106 - 3114
[30] DNA CLEAVAGE AND ANTITUMOR-ACTIVITY OF DESIGNED MOLECULES WITH CONJUGATED PHOSPHINE OXIDE-ALLENE-ENE-YNE FUNCTIONALITIES
NICOLAOU, KC
MALIGRES, P
SHIN, J
DELEON, E
RIDEOUT, D
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (21) : 7825 - 7826

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