Abstract
A synthesis of the unknown azacyclopropenone (azirinone) system was attempted via α-azido ketenes. Treatment of α-azido acid chlorides with triethylamine, in an attempt to generate α-azido ketenes, led in good yield to nitriles containing one less carbon. At -60° it was possible to trap the α-azido ketene 7c with benzalaniline to form a β-lactam. The formation of nitriles most likely proceeds by intermediacy of an azirinone. The sequence of reactions provides a useful degradation of carboxylic acids to nitriles with loss of one carbon.
Original language | English |
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Pages (from-to) | 1637-1641 |
Number of pages | 5 |
Journal | Tetrahedron |
Volume | 25 |
Issue number | 8 |
DOIs | |
State | Published - 1969 |
Externally published | Yes |