THE PYROLYSIS OF PHENYLNAPHTHALENEDICARBOXYLIC ANHYDRIDES - PRODUCTS OF RING CONTRACTION AND OF RADICAL CYCLIZATION

被引：31

作者：

ANDERSON, MR

BROWN, RFC

COULSTON, KJ

EASTWOOD, FW

WARD, A

机构：

[1] Department of Chemistry, Monash University, Clayton, VIC

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1990年 / 43卷 / 07期

关键词：

D O I：

10.1071/CH9901137

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Naphthalene-1, 2,-dicarboxylic anhydrides with neighbouring phenyl substituents give on flash vacuum pyrolysis (850-900°/0.02-0.04 mm) ring-contracted carbenes which insert into the phenyl groups. The 8-phenyl anhydride (7) gives acephenanthrylene (10) as the major product, and the 3-phenyl anhydride (15) gives 1, 2:4, 5-dibenzopentalene (indeno[2, l-a]indene) (18). The anhydrides (7) and (15) were synthesized by pyrolysis of the corresponding 1-naphthylmethyl propynoates (2) and (13) through a new one-step process of intramolecular Diels-Alder addition/retro-Diels-Alder elimination of acetylene. © 1990 ASEG.

引用

收藏

页码：1137 / 1150

页数：14

相关论文

共 25 条

[1] BETA-AROYLPROPIONIC ACIDS .10. CONVERSION OF GAMMA-ARYL-BETA-PHENYLBUTYRATES INTO POLYNUCLEAR COMPOUNDS [J].

BADDAR, FG ;

FLEIFEL, AM ;

SHERIF, S .

JOURNAL OF THE CHEMICAL SOCIETY, 1959, (MAR) :1009-1012

[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] FUSED CARBON RINGS .21. DIBENZOPENTALENE [J].

BLOOD, CT ;

LINSTEAD, RP .

JOURNAL OF THE CHEMICAL SOCIETY, 1952, (JUN) :2263-2268

[4] THE PYROLYSIS OF TETRAPHENYLPHTHALIC ANHYDRIDE - FORMATION OF 1,2,3-TRIPHENYLBENZOPENTALENE [J].

BROWN, RFC ;

COULSTON, KJ ;

EASTWOOD, FW ;

KORAKIS, T .

TETRAHEDRON LETTERS, 1988, 29 (51) :6791-6792

[5] METHYLENEKETENES AND METHYLENECARBENES .16. THE FORMATION OF DIPHENYLFURAN-2-ONES AND 3-PHENYLPHTHALIDE AS MINOR PRODUCTS OF THE PYROLYSIS OF DIPHENYLMETHYL PROPIOLATE [J].

BROWN, RFC ;

EASTWOOD, FW ;

CHAICHIT, N ;

GATEHOUSE, BM ;

PFEIFFER, JM ;

WOODROFFE, D .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (07) :1467-1481

[6] THE 1,2-DIDEHYDRONAPHTHALENE TO 1H-INDENYLIDENECARBENE REARRANGEMENT - FORMATION OF 7-METHYL-1H-INDENYLIDENEETHENONE AND ITS REARRANGEMENT TO ACENAPHTHYLEN-4-OL IN A FLASH VACUUM PYROLYTIC REACTION [J].

BROWN, RFC ;

COULSTON, KJ ;

DOBNEY, BJ ;

EASTWOOD, FW ;

FALLON, GD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1987, 40 (10) :1687-1694

[7] DETECTION OF THE 1,2-DIDEHYDRONAPHTHALENE TO 1H-INDENYLIDENECARBENE REARRANGEMENT BY INTRAMOLECULAR TRAPPING IN A FLASH VACUUM PYROLYTIC REACTION [J].

BROWN, RFC ;

COULSTON, KJ ;

EASTWOOD, FW ;

SAMINATHAN, S .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1987, 40 (01) :107-120

[8] ACETYLENIC ACIDS .1. REACTION OF ARYLPROPIOLIC ACIDS WITH CARBODIIMIDES [J].

CADBY, PA ;

HEARN, MTW ;

WARD, AD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1973, 26 (03) :557-570

[9] NOVEL CARBOCYCLIC DIANIONS - NMR-STUDY OF CHARGE DELOCALIZATION, PARATROPICITY, AND STRUCTURE IN THE DIANIONS OF ACEPHENANTHRYLENE AND ACEANTHRYLENE [J].

COHEN, Y ;

ROELOFS, NH ;

REINHARDT, G ;

SCOTT, LT ;

RABINOVITZ, M .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4207-4214

[10] BENZO[E]ISOBENZOFURAN - FORMATION AND REACTIONS OF THE PARENT AND ALKOXY-SUBSTITUTED DERIVATIVES [J].

CORNEJO, JJ ;

GHODSI, S ;

JOHNSON, RD ;

WOODLING, R ;

RICKBORN, B .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :3869-3876