Functionalized fluorinated arylethers by ring-opening of 1,2,3,4-tetrafluorodibenz[b,f][1,4]oxazepine

被引:4
作者
Doherty, B [1 ]
Nieuwenhuyzen, M [1 ]
Saunders, GC [1 ]
Sloan, MS [1 ]
机构
[1] Queens Univ Belfast, Sch Chem, Belfast BT9 5AG, Antrim, North Ireland
关键词
dibenzoxazepine; arylethers; crystal structure; ring-opening;
D O I
10.1016/S0022-1139(02)00245-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Treatment of 1,2,3,4-tetrafluorodibenz[b,f][1,4]oxazepine with acetyl or benzoyl chloride produces the fluorinated aryl ethers bearing amide and aldehyde functionalities, RCONHC6H4-2-OC6F4CHO-2 (2a R = Ph; 2b R = Me). The structures of intermediate compounds produced by addition of acid chloride across the imine bond and by partial hydrolyis of the resulting chlorine-containing compound have been determined. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:15 / 19
页数:5
相关论文
共 11 条
  • [1] Synthesis of polyfluorodibenz[b,f][1,4]oxazepines by the cyclization of 2-[(polyfluorobenzylidene)amino]phenols
    Allaway, CL
    Daly, M
    Nieuwenhuyzen, M
    Saunders, GC
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2002, 115 (01) : 91 - 99
  • [2] *BRUK AXS, 1998, SAINT NT PROGR DAT C
  • [3] COUTURE A, 1994, SYNTHESIS-STUTTGART, P953
  • [4] Desiraju G. R., 1999, The Weak Hydrogen Bond
  • [5] A TOTAL SYNTHESIS OF MAGALLANESINE - DMF ACETAL MEDIATED CYCLODEHYDRATION OF A METHYL KETONE THIOIMIDE
    FANG, FG
    FEIGELSON, GB
    DANISHEFSKY, SJ
    [J]. TETRAHEDRON LETTERS, 1989, 30 (21) : 2743 - 2746
  • [6] Attractive intramolecular edge-to-face aromatic interactions in flexible organic molecules
    Jennings, WB
    Farrell, BM
    Malone, JF
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (11) : 885 - 894
  • [7] X-H center dot center dot center dot pi(phenyl) interactions - Theoretical and crystallographic observations
    Malone, JF
    Murray, CM
    Charlton, MH
    Docherty, R
    Lavery, AJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1997, 93 (19): : 3429 - 3436
  • [8] CONFORMATIONAL INVERSION OF 2,3.6,7-DIBENZO-DERIVATIVES OF CYCLOHEPTATRIENE, TROPONE, HEPTAFULVENE, OXEPIN, THIEPIN, AND AZEPIN
    NOGRADI, M
    OLLIS, WD
    SUTHERLA.IO
    [J]. JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (03): : 158 - &
  • [9] PETRENKO NI, 1987, J FLUORINE CHEM, V36, P53
  • [10] Metalation chemistry of N-ethyl-N-(1-methoxy-2,2-dimethyl-propyl)benzamides. A new protective group for secondary amides
    Phillion, DP
    Walker, DM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (26) : 8417 - 8420