A m-benzyne to o-benzyne conversion through a 1,2-shift of a phenyl group

被引：19

作者：

Blake, ME ^{[1
]}

Bartlett, KL ^{[1
]}

Jones, M ^{[1
]}

机构：

[1] Princeton Univ, Dept Chem, Princeton, NJ 08544 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 21期

关键词：

D O I：

10.1021/ja0213672

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Pyrolysis of two differently labeled versions of 3-phenylphthalic anhydride shows that a m-benzyne can form the related o-benzyne through shift of a phenyl group. The highest energy point in the process is the transition structure for a reverse carbon-hydrogen insertion in an intermediate benzopentalene. With the minor addition of an intermediate alkyne formed through a Roger Brown rearrangement, the original mechanism for formation of acenaphthalene accommodates the labeling results.

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页码：6485 / 6490

页数：6

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共 42 条

[1] Formation of cyclopent[a]indene and acenaphthylene from allyl esters of biphenyl mono- and di-carboxylic acids and from biphenyl dicarboxylic anhydrides on flash vacuum pyrolysis at 1000-1100°C [J].

Bapat, JB ;

Brown, RFC ;

Bulmer, GH ;

Childs, T ;

Coulston, KJ ;

Eastwood, FW ;

Taylor, DK .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1997, 50 (12) :1159-1182

[2] OBSERVATION OF C-13 REARRANGEMENT IN [C-13(2)]BIPHENYLENE FORMED FROM BENZYNE ON PYROLYSIS OF [1,6-C-13(2)]PHTHALIC ANHYDRIDE AND "[2A,3-C-13(2)]BENZOCYCLOBUTENEDIONE [J].

BARRY, M ;

BROWN, RFC ;

EASTWOOD, FW ;

GUNAWARDANA, DA ;

VOGEL, C .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (08) :1643-1657

[3] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[4] 1,2-shifts of hydrogen atoms in aryl radicals [J].

Brooks, MA ;

Scott, LT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (23) :5444-5449

[5] METHYLENEKETENES AND METHYLENECARBENES .3. PYROLYTIC SYNTHESIS OF ARYLACETYLENES AND THEIR THERMAL REARRANGEMENTS INVOLVING ARYLMETHYLENECARBENES [J].

BROWN, RFC ;

EASTWOOD, FW ;

HARRINGT.KJ ;

MCMULLEN, GL .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1974, 27 (11) :2393-2402

[6]

BROWN RFC, 1988, RECL TRAV CHIM PAY B, V107, P655

[7] CYCLOPENT[A]INDENE (BENZOPENTALENE) AND PENTALENE - PYROLYTIC FORMATION FROM 3-PHENYL-PHTHALIC AND 3-VINYL-PHTHALIC ANHYDRIDES [J].

BROWN, RFC ;

CHOI, N ;

EASTWOOD, FW .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1995, 48 (02) :185-198

[8] CYCLOPENT[A]INDENE (BENZOPENTALENE) - GENERATION BY FLASH VACUUM PYROLYSIS AND SUBSEQUENT DIMERIZATION [J].

BROWN, RFC ;

CHOI, N ;

COULSTON, KJ ;

EASTWOOD, FW ;

WIERSUM, UE ;

JENNESKENS, LW .

TETRAHEDRON LETTERS, 1994, 35 (25) :4405-4408

[9] SCRAMBLING OF THE LABEL IN [C-13(2)] BIPHENYLENE OBTAINED ON PYROLYSIS OF [1,6,C-13(2)] AND [2,3,C-13(2)]-2-(3',3'-DIMETHYLTRIAZENYL)BENZOIC ACID [J].

BROWN, RFC ;

COULSTON, KJ ;

EASTWOOD, FW ;

VOGEL, C .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1988, 41 (11) :1687-1695

[10]

Brown RFC, 1999, EUR J ORG CHEM, V1999, P3211

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