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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

Batsanov, A., Brooke, G., Drury, C., Howard, J., & Lehmann, C. (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.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-BF36-9 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-BF37-7
Genre: Journal Article

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 Creators:
Batsanov, A.S.1, Author
Brooke, G.M.1, Author
Drury, C.J.1, Author
Howard, J.A.K.1, Author
Lehmann, C.W.1, 2, Author           
Affiliations:
1Chemistry Department, Science Laboratories, South Road, Durham DH 7 3L E, UK , ou_persistent22              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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 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.

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Language(s): eng - English
 Dates: 1994
 Publication Status: Issued
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1039/p19940001991
 Degree: -

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Title: Journal of the Chemical Society, Perkin Transactions 1
Source Genre: Journal
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Publ. Info: London : Royal Society of Chemistry
Pages: - Volume / Issue: (14) Sequence Number: - Start / End Page: 1991 - 1995 Identifier: ISSN: 1472-7781
CoNE: https://pure.mpg.de/cone/journals/resource/111053443082010_1