Ortho-vinylation reaction of phenols with ethyne

被引：32

作者：

Yamaguchi, M ^{[1
]}

Arisawa, M

Omata, K

Kabuto, K

Hirama, M

Uchimaru, T

机构：

[1] Tohoku Univ, Grad Sch Sci, Fac Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan

[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan

[3] MITI, Agcy Ind Sci & Technol, Dept Phys Chem, Natl Inst Mat & Chem Res, Tsukuba, Ibaraki 3058565, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 21期

关键词：

D O I：

10.1021/jo980785f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phenols were vinylated at the ortho-position with ethyne in the presence of SnCl4-Bu3N reagent. The reaction was applicable to phenols possessing either electron-donating or electron-withdrawing groups. 2,6-Divinylphenols were synthesized under modified conditions. A reaction mechanism involving carbostannylation of alkynyltin and phenoxytin was discussed.

引用

页码：7298 / 7305

页数：8

共 50 条

[1] UNSATURATED PHENOLS .2. ATTEMPTED SYNTHESES OF ORTHO-VINYLPHENOL [J].

BADER, AR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (15) :4155-4155

[2] PHOTOCHEMICAL REACTIONS .10. EXPERIMENTS WITH 1,3,5-CYCLOOCTATRIEN-7-ONE AND CYCLOOCTATETRAENE EPOXIDE [J].

BUCHI, G ;

BURGESS, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (16) :3104-&

[3] SILVER(I)-INDUCED COUPLING POLYMERIZATION OF BIFUNCTIONAL ORGANOBORON COMPOUNDS [J].

CHUJO, Y ;

TOMITA, I ;

KOZAWA, Y ;

SAEGUSA, T .

MACROMOLECULES, 1993, 26 (10) :2643-2644

[4] PREPARATION OF VINYLPHENOLS AND ISOPROPENYLPHENOLS [J].

CORSON, BB ;

HEINTZELMAN, WJ ;

SCHWARTZMAN, LH ;

TIEFENTHAL, HE ;

LOKKEN, RJ ;

NICKELS, JE ;

ATWOOD, GR ;

PAVLIK, FJ .

JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (04) :544-549

[5] SUBSTITUTED STYRENES .3. THE SYNTHESES AND SOME CHEMICAL PROPERTIES OF THE VINYLPHENOLS [J].

DALE, WJ ;

HENNIS, HE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (14) :3645-3649

[6]

DHEKNE VV, 1980, SYNTHESIS-STUTTGART, P58

[7] THE USE OF LIQUID PHASE OXIDATION FOR THE PREPARATION OF NUCLEARLY SUBSTITUTED STYRENES .2. PARA-VINYLPHENYL ACETATE [J].

EMERSON, WS ;

HEYD, JW ;

LUCAS, VE ;

COOK, WB ;

OWENS, GR ;

SHORTRIDGE, RW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, 68 (08) :1665-1666

[8] A FACILE GENERAL-ROUTE TO ENANTIOMERIC 1-(4-HYDROXYPHENYL)ALKANOLS, AND AN IMPROVED SYNTHESIS OF 4-VINYLPHENOL [J].

EVERHART, ET ;

CRAIG, JC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (07) :1701-1707

[9] The catalytic condensation of acetylene with phenols II Resorcinol [J].

Flood, SA ;

Nieuwland, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1928, 50 :2566-2573

[10] POLY[PARA-(FORMYLOXY)STYRENE] - SYNTHESIS AND RADIATION-INDUCED DECARBONYLATION [J].

FRECHET, JMJ ;

TESSIER, TG ;

WILLSON, CG ;

ITO, H .

MACROMOLECULES, 1985, 18 (03) :317-321

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