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Journal of the American Chemical Society

Gold-catalyzed formal [3 + 3] and [4 + 2] cycloaddition reactions of nitrosobenzenes with alkenylgold carbenoids.


PMID 22128862

Abstract

We report two new formal cycloaddition reactions between nitrosobenzenes and alkenylgold carbenoids. We obtained quinoline oxides 3 in satisfactory yields from the gold-catalyzed [3 + 3]-cycloadditions between nitrosobenzenes and alkenyldiazo esters 1. For propargyl esters 5, its resulting gold carbenes react with nitrosobenzene to give alkenylimine 8, followed by a [4 + 2]-cycloaddition with nitrosobenzene.

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N24609
Nitrosobenzene, ≥97%
C6H5NO