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Flash vacuum pyrolysis of 2-diazo-8-oxabicyclo[3.2.1]Oct-6-en-3-ones. A new method for the preparation of propadienones.

✍ Scribed by John C Brahms; William P Dailey

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
230 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

When diazoketones 3a and 3b are pyrolysed at 43oOC and 10S4 torr, they undergo loss of N2 followed by Wolff rearrangement and loss of furan by retro Diels-Alder reaction to yield the desired propadienones l(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, lb yields carbon monoxide and 2-butyne.

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