Tetrahedron Letters p. 19 - 22 (1986)
Update date:2022-07-29
Topics:
Koller, Manuel
Karpf, Martin
Dreiding, Andre S.
The gas flow thermolyses of 1-isobutenyl alkynyl and 2-methylphenyl alkynyl ketones were found to lead to phenols and to cyclopentenones.The results are explained by a 5-ring carbene process (the known α-alkynone cyclization) and a 6-ring as well as a 5-ring addition process.The latter two (novel) processes are thought to be intramolecular "C-H to C<*>C additions" in two directions.The 5-ring addition process was used in a short (but low yield) synthesis of methylenomycin B.
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Doi:10.1021/om800073s
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(2008)Doi:10.1002/hlca.19580410624
(1958)Doi:10.1021/jm500373x
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(2008)Doi:10.1021/jo00370a025
(1986)
