THE PYROLYSIS OF 1,3,4,5,6,7,8-HEPTAFLUORO-2-NAPHTHYL PROPYNOATE - REMARKABLE PRODUCTS OBTAINED VIA AN INTERNAL DIELS-ALDER REACTION

Authors
BATSANOV AS BROOKE GM DRURY CJ HOWARD JAK LEHMANN CW
Citation
As. Batsanov et al., THE PYROLYSIS OF 1,3,4,5,6,7,8-HEPTAFLUORO-2-NAPHTHYL PROPYNOATE - REMARKABLE PRODUCTS OBTAINED VIA AN INTERNAL DIELS-ALDER REACTION, Journal of the Chemical Society. Perkin transactions. I, (14), 1994, pp. 1991-1995
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
14
Year of publication
1994
Pages
1991 - 1995
Database
ISI
SICI code
0300-922X(1994):14<1991:TPO1P->2.0.ZU;2-R
Abstract
Flash vacuum pyrolysis of the ester 1,3,4,5,6,7,8-heptafluoro-2-naphth yl propynoate (6) at 550 degrees C/0.01 mmHg gave three products: 3 an d 4 by an overall decarbonylation reaction. and 5 by a further decarbo nylation of 3 and/or 4. Isomerisation of 6 to 2-fluoropropynyl 2-napht hoate 8 by a Diels-Alder/retro-Diels-Alder sequence followed by decarb onylation and a series of 1,2-fluorine shifts offers a rationalisation for the formation of the products.