GAS-PHASE GENERATION AND CYCLIZATION REACTIONS OF SOME ORTHOSUBSTITUTED PHENYL RADICALS

被引:22
作者
CADOGAN, JIG [1 ]
HUTCHISON, HS [1 ]
MCNAB, H [1 ]
机构
[1] UNIV EDINBURGH,DEPT CHEM,EDINBURGH EH9 3JJ,MIDLOTHIAN,SCOTLAND
关键词
D O I
10.1016/S0040-4020(01)90385-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Flash vacuum pyrolysis of the allyl esters 2 (X=O,S, CH2, CO) at 900-degrees-C (10(-2) Torr) gives dibenzofurans, dibenzothiophenes, fluorenes, and fluorenones respectively as the major products. The mechanism involves the phenyl radical intermediates 1 which equilibrate by intramolecular hydrogen transfer via six-membered transition states, prior to cyclisation.
引用
收藏
页码:7747 / 7762
页数:16
相关论文
共 37 条
  • [1] ALLEN CFH, 1943, ORG SYNTH COLL, V2, P15
  • [2] AMES DE, 1983, SYNTHESIS-STUTTGART, P234
  • [3] DIRECT BRADSHER REACTION .3. NEW METHOD FOR BENZOLOGATION OF HETEROCYCLES
    ASHBY, J
    AYAD, M
    METHCOHN, O
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (14): : 1744 - 1747
  • [4] DEHYDROGENATION OF TETRAHYDROCARBAZOLES BY CHLORANIL
    BARCLAY, BM
    CAMPBELL, N
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1945, : 530 - 533
  • [5] A SHORT SYNTHESIS OF DIBENZOFURANS AND DIBENZOTHIOPHENES
    BLACK, M
    CADOGAN, JIG
    MCNAB, H
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (05) : 395 - 396
  • [6] ORIENTATION IN SOME FRIEDEL-CRAFTS ACYLATIONS OF 2,2]-DIMETHOXYBIPHENYL + CYCLIZATION OF REACTION PRODUCTS
    BUUHOI, NP
    THANG, DC
    PETIT, L
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (03) : 762 - &
  • [7] GAS-PHASE REACTIONS OF 2-BENZYL RADICAL AND 2-BENZOYL-PHENOXYL RADICAL, AND OF 2-PHENOXYBENZYL RADICALS - EXAMPLES OF NEW HYDROGEN-TRANSFER PROCESSES
    CADOGAN, JIG
    HUTCHISON, HS
    MCNAB, H
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02): : 385 - 393
  • [8] THERMAL INTERCONVERSION AND CYCLIZATION REACTIONS OF 2-(ARYLTHIO)BENZYL RADICALS AND 2-(BENZYL)THIOPHENOXYL RADICALS
    CADOGAN, JIG
    HUTCHISON, HS
    MCNAB, H
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (10): : 2875 - 2879
  • [9] SHORT CONTACT TIME REACTIONS OF LARGE ORGANIC FREE-RADICALS
    CADOGAN, JIG
    HICKSON, CL
    MCNAB, H
    [J]. TETRAHEDRON, 1986, 42 (08) : 2135 - 2165
  • [10] NMR SPECTRA OF SOME SUBSTITUTED DIBENZOTHIOPHENES
    CAMPAIGNE, E
    ASHBY, J
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1969, 6 (04) : 517 - +