Theoretical evidence for oxygenated intermediates in the reductive cyclization of nitrobenzenes |
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Authors: | Davies Ian W Guner Vildan A Houk K N |
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Affiliation: | Department of Process Research, Merck & Co. Inc., Rahway, NJ 07065-0900, USA. ian_davies1@merck.com |
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Abstract: | Deoxygenation of nitroaromatics is a classic synthetic method for the construction of nitrogen heterocycles. The generally accepted mechanism involves exhaustive deoxygenation to a singlet nitrene. We present theoretical evidence for an alternative, 6pi-electron 5-atom electrocyclization of nitroso-styrenes, -stilbenes, and -biphenyls to nitronates. A downstream 1,5-H shift and tautomerization leads to N-hydroxy heterocycles. [reaction: see text] |
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