Abstract
Vinyl azides undergo slow cycloaddition with diphenylketene (2) leading to five-membered ring enamino ketones 6 with loss of N2. The reaction appears to involve nucleophilic attack of the β carbon from the vinyl azide upon the ketene. A substantial improvement in yield of 6 is achieved by generating 2 in situ from a diazo ketone in solution. Treatment of the enamino ketones with phosphorus pentachloride or chlorine leads to a chlorination. In the case of 2-azido-1-hexene, cycloaddition with 2 proceeds with formation of cyclobutanones.
Original language | English |
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Pages (from-to) | 2682-2685 |
Number of pages | 4 |
Journal | Journal of Organic Chemistry |
Volume | 37 |
Issue number | 17 |
DOIs | |
State | Published - 1 Aug 1972 |
Externally published | Yes |