EVIDENCE FOR THE FORMATION OF 1,3-DEHYDROBENZENE DIRADICALS BY SILICON SHIFT IN 1,4-DEHYDROBENZENES AT HIGH-TEMPERATURE

被引：36

作者：

JOHNSON, GC

STOFKO, JJ

LOCKHART, TP

BROWN, DW

BERGMAN, RG

机构：

[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720

[2] CALTECH,DIV CHEM & CHEM ENGN,PASADENA,CA 91125

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 23期

关键词：

D O I：

10.1021/jo01337a051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Evidence is presented that high temperature pyrolysis of three isomeric disubstituted 1,5-hexadiyn-3-enes proceeds by initial cyclization to 1,4-dehydrobenzene intermediates, and that these initially formed species are capable of rearranging to 1,3-dehydrobenzenes. Both types of intermediates appear to behave as diradicals at these temperatures. © 1979, American Chemical Society. All rights reserved.

引用

页码：4215 / 4218

页数：4

共 11 条

[1] REACTIVE 1,4-DEHYDROAROMATICS
BERGMAN, RG
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (01) : 25 - 31
[2] BRESLOW R, 1977, TETRAHEDRON LETT, P3429
[3] BRESLOW R, 1976, J AM CHEM SOC, V98, P5703
[4] BRUNTON G, 1978, J AM CHEM SOC, V100, P4197, DOI 10.1021/ja00481a031
[5] KINETIC APPLICATIONS OF ELECTRON-PARAMAGNETIC RESONANCE SPECTROSCOPY .26. QUANTUM-MECHANICAL TUNNELING IN ISOMERIZATION OF STERICALLY HINDERED ARYL RADICALS
BRUNTON, G
GRILLER, D
BARCLAY, LRC
INGOLD, KU
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (22) : 6803 - 6811
[6] SUBSTITUTED BENZOCYCLOBUTENES, INDANS, AND TETRALINS VIA COBALT-CATALYZED COOLIGOMERIZATION OF ALPHA,OMEGA-DIYNES WITH SUBSTITUTED ACETYLENES - FORMATION AND SYNTHETIC UTILITY OF TRIMETHYLSILYLATED BENZOCYCLOALKENES
HILLARD, RL
VOLLHARDT, KPC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (12) : 4058 - 4069
[7] PARA BENZYNE - GENERATION AS AN INTERMEDIATE IN A THERMAL ISOMERIZATION REACTION AND TRAPPING EVIDENCE FOR 1,4-BENZENEDIYL STRUCTURE
JONES, RR
BERGMAN, RG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (02) : 660 - &
[8] EQUILIBRIUM GEOMETRIES AND RELATIVE ENERGIES OF THE LOWEST SINGLET AND TRIPLET-STATES OF ORTHO-BENZYNE,META-BENZYNE, AND PARA-BENZYNE
NOELL, JO
NEWTON, MD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (01) : 51 - 57
[9] SYNTHESIS, PROPERTIES, AND REACTIONS OF DISPIRO[2.2.2.2]DECA-4,9-DIENE
TSUJI, T
SHIBATA, T
HIENUKI, Y
NISHIDA, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (06) : 1806 - 1814
[10] SYNTHESIS AND REACTIONS OF BICYCLO[3.1.0]HEXATRIENES
WASHBURN, WN
ZAHLER, R
CHEN, I
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (18) : 5863 - 5874

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