Oxidative Synthesis of α,β-Unsaturated Ketone from α-Iodo Ketone Using Peracid

Abstract

Oxidation of α-iodo ketone in CH₂Cl₂ using m-chloro­perbenzoic acid yields α,β-unsaturated ketone by β-H elimination in good yield. This reaction affords a new and convenient synthetic method for α,β-unsaturated ketone from α-iodo ketone.

α-iodo ketone - oxidation - elimination reaction - α,β-unsaturated ketone

References

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The starting material α-iodo cyclic ketones used in our experiments were prepared according to the literature procedures. [11] The physical data of typical compound 3,4-dihydro-2-iodo-1(2H)-naphthalenone (9) is listed.
Colorless needles; mp 78.5-79.6 °C.
IR (KBr): 1672, 1593 cm^-1.
¹H NMR (CDCl₃): δ = 5.02 (t, J = 3.7 Hz, 1 H, C2), 7.31 (m, 2 H), 7.51 (m, 1 H), 8.09 (d, J = 7.7 Hz, 1 H).
¹³C NMR (CDCl₃): δ = 27.8, 30.7, 32.7, 127.0, 128.7, 128.8, 129.4, 134.0, 142.8, 191.8.
HRMS: m/z calcd for C₁₀H₉OI [M]: 271.9699; found: 271.9734.

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