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Synlett 2005(3): 421-424
DOI: 10.1055/s-2004-837218
DOI: 10.1055/s-2004-837218
LETTER
© Georg Thieme Verlag Stuttgart · New YorkHighly 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
Weitere Informationen
Received
8 November 2004
Publikationsdatum:
17. Dezember 2004 (online)
Publikationsverlauf
Publikationsdatum:
17. Dezember 2004 (online)
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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References
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.