Tetrahedron Letters p. 1381 - 1384 (1990)
Update date:2022-08-22
Topics:
Brahms
Dailey
When diazoketones 3a and 3b are pyrolysed at 430°C and 10-4 torr, they undergo loss of N2 followed by Wolff rearrangement and loss of furan by retro Diels-Alder reaction to yield the desired propadienones 1(a,b). If argon is added to the pyrolysate mixture, these reactive compounds can be trapped under matrix isolation conditions at 22 K and observed by FTIR. Upon photolysis, 1b yields carbon monoxide and 2-butyne.
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