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
Batsanov, AS
Brooke, GM
Holling, D
Kenwright, AM
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