Highly Efficient and Stereoselective Construction of 1-Iodo- or 1-Phenyl­selenenyl-2-aryl-3-oxabicyclo[3.1.0]hexane from the Reaction of Arylmethyl­idenecyclopropylcarbinols with Iodine or Diphenyldiselenide

Abstract

The reaction of arylmethylidenecyclopropylcarbinols 1 with iodine in the presence of potassium carbonate or diphenyldi­selenide in the presence of sulfuryl chloride stereoselectively gives ring-closure product 1-iodo-2-aryl-3-oxabicyclo[3.1.0]hexane or 1-phenylselenenyl-2-aryl-3-oxabicyclo[3.1.0]hexane in good to high yields at room temperature. A plausible reaction mechanism has been proposed.

arylmethylidenecyclopropylcarbinols - diphenyldi­selenide - sulfuryl chloride - ring-opening reaction - 1-iodo-2-aryl-3-oxabicyclo[3.1.0]hexane - cyclization - 1-phenylselenenyl-2-aryl-3-oxabicyclo[3.1.0]hexane

References

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<A NAME="RU31104ST-8">8</A>

The crystal data of 2g has been deposited in CCDC with number 244085. Empirical Formula: C₁₄H₁₇O₄I; formula weight: 376.18; crystal color, habit: colorless, prismatic; crystal system: triclinic; lattice type: primitive; lattice parameters: a = 7.2860 (7) Å, b = 10.4129 (10) Å, c = 10.9412 (11) Å, α = 65.775 (2)°, β = 87.581 (2)°, γ = 72.222 (2)°, V = 717.54 (12) ų; space group: P-1; Z = 2; D _calc = 1.741 g/cm³; F ₀₀₀ = 372; diffractometer: Rigaku AFC7R; residuals: R; Rw: 0.0434, 0.1079.

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