Pyrolytic chemistry of (1-isonaphthofuryl)methyl benzoate

Flash vacuum pyrolysis of (1-isonaphthofuryl)methyl benzoate ( 6) at temperatures in the range 550–700 °C and ca. 10 −2 torr gave methylenenaphthocyclobutenone ( 13), 3-ethynyl-2-naphthaldehyde ( 14) and naphthocyclopentadienone ( 15). The mechanism for the formation of 13–15 is proposed to involve...

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Bibliographic Details
Published in:Tetrahedron letters 1998-10, Vol.39 (40), p.7381-7384
Main Authors: Chen, Ping-Shu, Tai, Chia-Liang, Chou, Chin-Hsing
Format: Article
Language:English
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Summary:Flash vacuum pyrolysis of (1-isonaphthofuryl)methyl benzoate ( 6) at temperatures in the range 550–700 °C and ca. 10 −2 torr gave methylenenaphthocyclobutenone ( 13), 3-ethynyl-2-naphthaldehyde ( 14) and naphthocyclopentadienone ( 15). The mechanism for the formation of 13–15 is proposed to involve double migrations of the benzoate group into the isonaphthofuran ring. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)01601-3