An unusual non-radical phenolic coupling

被引:6
作者
Bell, NV
Bowman, WR
Coe, PF
Turner, AT
Whybrow, D
机构
[1] LOUGHBOROUGH UNIV TECHNOL, DEPT CHEM, LOUGHBOROUGH LE11 3TU, LEICS, ENGLAND
[2] KNOLL PHARMACEUT, CHEM DEV GRP, NOTTINGHAM NG1 1GF, ENGLAND
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4039(97)00407-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4-Substituted-2,6-diiodophenols undergo non-radical ortho-ortho phenolic coupling by an S(N)2 mechanism with liberation of I-2 to yield the corresponding biphenyls. in particular, the ethyl ester of N-acetyl-3,5-diiodotyrosine gives good yields of the corresponding dityrosine analogue 2 under mild conditions. (C) 1997 Published by Elsevier Science Ltd.
引用
收藏
页码:2581 / 2584
页数:4
相关论文
共 16 条
[1]  
AESCHBACH R, 1975, Mitteilungen aus dem Gebiete der Lebensmitteluntersuchung und Hygiene, V66, P85
[2]   (ETA-6-BENZENE)(ETA-5-ETHYLTETRAMETHYLCYCLOPENTADIENYL)RHODIUM (III) HEXAFLUOROPHOSPHATE - A REAGENT FOR CATALYTIC PHENOL OXIDATIVE COUPLING [J].
BARRETT, AGM ;
ITOH, T ;
WALLACE, EM .
TETRAHEDRON LETTERS, 1993, 34 (14) :2233-2234
[3]   THE REACTIVITY OF OXYGEN NUCLEOPHILES WITH ARYL RADICALS IN THE S(RN)1 MECHANISM [J].
BAUMGARTNER, MT ;
PIERINI, AB ;
ROSSI, RA .
TETRAHEDRON LETTERS, 1992, 33 (17) :2323-2326
[4]   NUCLEOPHILIC COUPLING OF ALKALI 2-NAPHTHOXIDES WITH 1-BROMO-2-NAPHTHOLS - ION-PAIRING AND HALOGEN DANCE IN THE FORMATION OF 1,1'-BINAPHTHALENE-2,2'-DIOLS [J].
BELOHRADSKY, M ;
HOLY, P ;
ZAVADA, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (10) :1853-1856
[5]   REACTIVITY OF HALOGENONAPHTHOLS TOWARDS NUCLEOPHILES .2. KINETICS AND MECHANISMS OF REACTIONS OF 1-HALOGENO-2-NAPHTHOLS WITH ANILINES [J].
BOSCO, M ;
TODESCO, PE .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1970, (09) :1742-&
[6]  
ECKHOLM R, 1990, INT REV CYTOL, V120, P243
[7]   SELF-CONDENSATION OF 1-BROMO-2-NAPHTHOL - MECHANISM OF FORMATION OF A 1,4-DINAPHTHODIOXIN [J].
FORLANI, L ;
LUGLI, A ;
NANNI, D ;
TODESCO, PE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (06) :1291-1293
[8]   SYNTHESIS OF PIPERAZINOMYCIN, A NOVEL ANTIFUNGAL ANTIBIOTIC [J].
NISHIYAMA, S ;
NAKAMURA, K ;
SUZUKI, Y ;
YAMAMURA, S .
TETRAHEDRON LETTERS, 1986, 27 (37) :4481-4484
[9]   SYNTHESES OF ISODITYROSINE, DITYROSINE AND RELATED-COMPOUNDS BY PHENOLIC OXIDATION OF TYROSINE AND PHENYLGLYCINE DERIVATIVES USING AN ELECTROCHEMICAL METHOD [J].
NISHIYAMA, S ;
KIM, MH ;
YAMAMURA, S .
TETRAHEDRON LETTERS, 1994, 35 (45) :8397-8400
[10]   TOTAL SYNTHESIS OF BASTADINS [J].
NISHIYAMA, S ;
YAMAMURA, S .
TETRAHEDRON LETTERS, 1982, 23 (12) :1281-1284