TiCl4, dioxane -: A facile and efficient system for De-O-benzylation, De-O-xylyallylation, and De-O-allylation of phenolic ethers

被引:13
作者
Rajakumar, P [1 ]
Murali, V [1 ]
机构
[1] Univ Madras, Dept Organ Chem, Madras 600025, Tamil Nadu, India
关键词
D O I
10.1081/SCC-120026311
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Simultaneous de-O-xylylation and reductive coupling was observed when I equiv. of the dialdehyde 2a/2b was treated with 5 equiv. of each TiCl4 and Zinc which lead to the development of TiCl4 in dioxane as a new system for the facile deprotection of phenolic ethers 4a-4d, 5a-5d, and 6a-6c.
引用
收藏
页码:3891 / 3896
页数:6
相关论文
共 31 条
  • [1] ALCL3-N,N-DIMETHYLANILINE - A NEW BENZYL AND ALLYL ETHER CLEAVAGE REAGENT
    AKIYAMA, T
    HIROFUJI, H
    OZAKI, S
    [J]. TETRAHEDRON LETTERS, 1991, 32 (10) : 1321 - 1324
  • [2] A general procedure of the peptide synthesis.
    Bergmann, M
    Zervas, L
    [J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1932, 65 (07): : 1192 - 1201
  • [3] Chen FE, 2001, SYNTHESIS-STUTTGART, P1772
  • [4] Falck JR, 2001, ANGEW CHEM INT EDIT, V40, P1281, DOI 10.1002/1521-3773(20010401)40:7<1281::AID-ANIE1281>3.0.CO
  • [5] 2-B
  • [6] New developments in the chemistry of low-valent titanium
    Furstner, A
    Bogdanovic, B
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (21): : 2442 - 2469
  • [7] GREEN TW, 1991, PROTECTIVE GROUPS OR
  • [8] Total synthesis of microcarpalide
    Gurjar, MK
    Nagaprasad, R
    Ramana, CV
    [J]. TETRAHEDRON LETTERS, 2003, 44 (14) : 2873 - 2875
  • [9] STEREOSELECTIVE TOTAL SYNTHESIS OF GUAIAZULENIC SESQUITERPENOIDS ALPHA-BULNESENE AND BULNESOL
    HEATHCOC.CH
    RATCLIFF.R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (07) : 1746 - &
  • [10] REGIOSELECTIVE DE-O-BENZYLATION WITH LEWIS-ACIDS
    HORI, H
    NISHIDA, Y
    OHRUI, H
    MEGURO, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) : 1346 - 1353