Metal-assisted reactions .26. Catalytic reactivity and ether bond lengths in aryloxytetrazoles and aryloxypseudosaccharins

被引：22

作者：

Alves, JAC ^{[1
]}

Barkley, JV ^{[1
]}

Brigas, AF ^{[1
]}

Johnstone, RAW ^{[1
]}

机构：

[1] UNIV LIVERPOOL,DEPT CHEM,LIVERPOOL L69 3BX,MERSEYSIDE,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1997年 / 04期

关键词：

D O I：

10.1039/a607912a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

X-Ray structure determinations on a variety of aryloxytetrazoles 1 and aryloxypseudosaccharins 4 have shown that the central C-O-C ether linkage is remarkable in having one very long C-O bond and one very short one. The central C-O-C bond angle is close to 120 degrees. The implications of these effects on the reactivity of compounds 1 and 4 towards catalytic hydrogenolysis or cross-coupling are explored.

引用

页码：669 / 677

页数：9

共 39 条

[1] TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].

ALLEN, FH ;

KENNARD, O ;

WATSON, DG ;

BRAMMER, L ;

ORPEN, AG ;

TAYLOR, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19

[2] 3-(1-naphthyloxy)-1,2-benzisothiazole 1,1-dioxide: Electronic effects of conjugation [J].

Alves, JAC ;

Brigas, AF ;

Johnstone, RAW .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 :1576-1579

[3] STRUCTURAL CHEMISTRY OF DONOR-ACCEPTOR INTERACTIONS [J].

BENT, HA .

CHEMICAL REVIEWS, 1968, 68 (05) :587-&

[4] OBSERVATION OF BURST KINETICS IN HETEROGENEOUS CATALYTIC TRANSFER HYDROGENOLYSIS [J].

BETHELL, D ;

JOHNSTONE, RAW ;

PRICE, PJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (05) :303-304

[5] TRANSITION-METAL-CATALYZED IPSO-REPLACEMENT REACTIONS OF HETEROAROMATIC PHENOLIC ETHERS BY ZINC AND TIN ORGANOMETALLIC COMPOUNDS [J].

BRIGAS, AF ;

JOHNSTONE, RAW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (17) :1923-1924

[6] METAL-ASSISTED REACTIONS .20. CATALYTIC TRANSFER HYDROGENOLYSIS OF PHENOLIC C-O BONDS [J].

BRIGAS, AF ;

JOHNSTONE, RAW .

TETRAHEDRON LETTERS, 1990, 31 (40) :5789-5790

[7] 3-(4-methoxyphenoxy)-1,2-benzisothiazole 1,1-dioxide: Its relation to mechanistic behaviour in catalytic transfer hydrogenolysis [J].

Brigas, AF ;

Johnstone, RAW .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 :1293-1296

[8] METAL-ASSISTED REACTIONS .24. THE IMPORTANCE OF SOLVENTS IN LIQUID-PHASE HETEROGENEOUS CATALYTIC TRANSFER REDUCTION [J].

BRIGAS, AF ;

JOHNSTONE, RAW .

TETRAHEDRON, 1992, 48 (36) :7735-7746

[9] GEOMETRICAL REACTION COORDINATES .2. NUCLEOPHILIC ADDITION TO A CARBONYL GROUP [J].

BURGI, HB ;

DUNITZ, JD ;

SHEFTER, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (15) :5065-5067

[10]

BURGI HB, 1987, J AM CHEM SOC, V109, P2924, DOI 10.1021/ja00244a012

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