Synlett p. 723 - 726 (2018)
Update date:2022-08-05
Topics:
Shima, Yusuke
Igarashi, Emiko
Yoshimura, Tomoyuki
Matsuo, Jun-Ichi
Formal [4+2] cycloaddition between 3-ethoxy-2-alkylcyclobutanones and nitrosobenzene proceeded by activation with Me 3 SiOTf to afford 6-alkyl-2-phenyl-2 H -1,2-oxazin-5(6 H)-one by regioselective cleavage of the more substituted C2-C3 bond of the cyclobutanone ring. On the other hand, reactions of 3-phenylcyclobutanones and 2-benzyloxycyclobutanone with nitrosobenzene gave γ,δ-unsaturated and cyclic hydroxamic acid derivatives, respectively, by cleavage of a cyclobutanone C1-C2 bond.
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