Pyrolysis reactions of nonafluorobiphenyl-4-yl prop-2-enyl ether: a remarkable rearrangement reaction of an intramolecular Diels-Alder product

被引：4

作者：

Batsanov, AS ^{[1
]}

Brooke, GM ^{[1
]}

Holling, D ^{[1
]}

Kenwright, AM ^{[1
]}

机构：

[1] Univ Durham, Dept Chem, Sci Labs, Durham DH1 3LE, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 11期

关键词：

D O I：

10.1039/b001356k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compound 16 on flash vapour pyrolysis (FVP) at 350 degrees C gives a complex mixture which includes 20, the product of one of the two possible intramolecular Diels-Alder reactions of the cyclohexa-2,4-dienone intermediate 17 formed via a Claisen rearrangement reaction. FVP of 16 at 420 degrees C gives the bicyclic compound 30, formed not from the other possible Diels-Alder adduct 27 but from an isomer 31 having exactly the same carbon skeleton, but produced as a transient intermediate via a rare retro-cyclisation reaction of 20 to a tethered ketene 32 and recyclisation via the alternative mode.

引用

页码：1731 / 1734

页数：4

共 12 条

[1] Pyrolysis reactions of 4-nonafluorobiphenyl prop-2-enyl ether: a remarkable rearrangement reaction [J].

Batsanov, AS ;

Brooke, GM ;

Holling, D ;

Kenwright, AM .

CHEMICAL COMMUNICATIONS, 1999, (16) :1549-1550

[2] PARTIALLY FLUORINATED HETEROCYCLIC-COMPOUNDS .17. THE PREPARATION OF FUSED 2H-PYRAN DERIVATIVES FROM POLYFLUOROARYL AND HETEROARYL PROP-2-ENYL ETHERS WITH POTASSIUM FLUORIDE VIA AN ELECTROCYCLIZATION REACTION - A NOVEL [1,5] SIGMATROPIC PROTON SHIFT DURING THE REACTION OF PENTAFLUOROPHENYL PROP-2-ENYL SULFIDE WITH POTASSIUM FLUORIDE [J].

BROOKE, GM .

JOURNAL OF FLUORINE CHEMISTRY, 1983, 22 (05) :483-491

[3] PYROLYSES OF PENTAFLUOROPHENYL PROP-2-ENYL AND [2,3,3-H-2(3)]PROP-2-ENYL ETHERS - FORMATION OF 1-FLUOROVINYL 2,3,4-TRIFLUOROPHENYL KETONES VIA INTERNAL DIELS-ALDER REACTIONS [J].

BROOKE, GM ;

HALL, DH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (13) :1463-1465

[4]

BROOKE GM, 1971, TETRAHEDRON LETT, P2377

[5]

BROOKE GM, 1978, J CHEM SOC PERK T 1, P780, DOI 10.1039/p19780000780

[6] 2,3,4,5,7-PENTAFLUOROTRICYCLO(3.3.1.02,7) NON-3-EN-6-ONE, AN INTERNAL DIELS-ALDER ADDUCT FROM THE CLAISEN REARRANGEMENT INTERMEDIATE FROM PENTAFLUOROPHENYL PROP-2-ENYL ETHER [J].

BROOKE, GM ;

HALL, DH .

JOURNAL OF FLUORINE CHEMISTRY, 1982, 20 (02) :163-166

[7]

BROOKE GM, 1974, J CHEM SOC PERK T 1, P233, DOI 10.1039/p19740000233

[8]

BUXTON MW, 1972, J FLUORINE CHEM, V2, P231

[9]

Hyatt J., 1994, ORG REACTIONS, V45, P159

[10]

MUJASHI T, 1979, TETRAHEDRON LETT, P155

← 1 2 →