79655-74-6Relevant academic research and scientific papers
The Gas-Flow Thermolysis of 1-Isobutenyl Alkynyl and 2-Methylphenyl Alkynyl Ketones. Synthesis of Methylenomycin B
Koller, Manuel,Karpf, Martin,Dreiding, Andre S.
, p. 560 - 579 (1986)
The gas-flow thermolysis of 1-isobutenyl alkynyl or 2-methyphenyl alkynyl ketones were found to lead to phenols and cyclopentenones or to naphthols and indanones, respectively.These conversions involve two cyclization processes so far unknown with α-alkynones; they are interpreted as intramolecular additions of an allylic or a benzylic C,H bond to a triple bond which may occur in two directions.In addition, the cyclopentenones formed by the α-alkynone cyclization, a known carbene process yielding 5-rings, were also found.The available evidence ruled out a carbene process yielding 6-rings.The addition process yielding 5-rings was applied to a short (but low yield) synthesis of methylenomycin B.
THE FLOW THERMOLYSES OF 1-ISOBUTENYL ALKYNYL- AND 2-METHYLPHENYL ALKYNYL KETONES. SYNTHESIS OF METHYLENOMYCIN B
Koller, Manuel,Karpf, Martin,Dreiding, Andre S.
, p. 19 - 22 (2007/10/02)
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 CC additions" in two directions.The 5-ring addition process was used in a short (but low yield) synthesis of methylenomycin B.
