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The pyrolysis of 1,3,4,5,6,7,8-heptafluoro-2-naphthyl propynoate: remarkable products obtained via an internal Diels–Alder reaction

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Citation

Batsanov, A. S., Brooke, G. M., Drury, C. J., Howard, J. A. K., & Lehmann, C. W. (1994). 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 1, (14), 1991-1995. doi:10.1039/p19940001991.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0024-BF36-9
Abstract
Flash vacuum pyrolysis of the ester 1,3,4,5,6,7,8-heptafluoro-2-naphthyl propynoate (6) at 550 °C/0.01 mmHg gave three products: 3 and 4 by an overall decarbonylation reaction. and 5 by a further decarbonylation of 3 and/or 4. Isomerisation of 6 to 2-fluoropropynyl 2-naphthoate 8 by a Diels-Alder/retro-Diels-Alder sequence followed by decarbonylation and a series of 1,2-fluorine shifts offers a rationalisation for the formation of the products.