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

Bao-Yu Wang; Jin-Wen Huang; Le-Ping Liu; Min Shi

doi:10.1055/s-2004-837218

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Synlett 2005(3): 421-424
DOI: 10.1055/s-2004-837218

LETTER

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

Bao-Yu Wang^a, Jin-Wen Huang^b, Le-Ping Liu^b, Min Shi*^b
^a Department of Chemistry, School of Science and Technology, Yanbian University, Yanji, Jilin Province 133002, P. R. China
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China
e-Mail: Mshi@pub.sioc.ac.cn;

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Publication History

Received 8 November 2004
Publication Date:
17 December 2004 (online)

Abstract
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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.

Key words

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

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8

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) Å³; 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.