Reactions of Nitrosobenzenes with Cyclobutanones by Activation with a Lewis Acid

Published as part of the Cluster C–C Activation
Dedicated to Professor Teruaki Mukaiyama in celebration of his 90th birthday

Abstract

Formal [4+2] cycloaddition between 3-ethoxy-2-alkylcyclobutanones and nitrosobenzene proceeded by activation with Me₃SiOTf to afford 6-alkyl-2-phenyl-2H-1,2-oxazin-5(6H)-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.

Key words

cyclobutanone - nitrosobenzene - cycloaddition - Lewis acid - carbon–carbon bond cleavage - hydroxamic acid

• References and Notes

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• 26 6-tert-Butyl-2-phenyl-2H-1,2-oxazin 5(6H)-one (2a) – Typical Procedure To a stirred mixture of cyclobutanone 1a (143 mg, 0.84 mmol) and nitrosobenzene (30 mg, 0.28 mmol) in CH₂Cl₂ (2 mL) was added Me₃SiOTf (0.17 mL, 0.92 mmol) at r.t. The reaction mixture was stirred for 10 min. The reaction was quenched by addition of potassium sodium tartrate. The mixture was extracted with EtOAc, and the organic extracts were washed with brine, dried over anhydrous Na₂SO₄, filtered, and concentrated. The crude product was purified by preparative thin-layer chromatography on silica gel (hexane/Et₂O = 1:2) to afford 2a (43.6 mg, 0.19 mmol, 67%) as a brown solid; mp 69.0–70.0 °C. ¹H NMR (600 MHz, CDCl₃): δ = 1.16 (s, 9 H), 4.20 (s, 1 H), 5.34 (d, J = 7.2 Hz, 1 H), 7.14 (t, J = 7.5 Hz, 1 H), 7.22 (d, J = 8.4 Hz, 2 H), 7.40 (t, J = 8.1 Hz, 2 H), 7.71 (d, J = 7.8 Hz, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 26.7, 34.7, 91.2, 99.3, 114.5, 124.4, 129.5, 139.8, 140.6, 188.1. IR (CHCl₃): 3018, 1576, 1223, 1209 cm^–1. HRMS: m/z calcd for C₁₄H₁₈NO₂: 232.13375; found: 232.13476.