ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of Bis(1-phenoxy-propen-2-yl)-sulfanes derived from Bis(1-chloro-3-phenoxy-prop-2-yl)-sulfanes with Potassium-tert.-butoxid - Determination of the E,E-ConfigurationBis(1-chloro-3-phenoxy-prop-2-yl)-sulfanes (1), anti-MARKOVNIKOV 2:1-adducts of allylphenyl ethers with sulfur dichloride at low temperature are transformed in the presence of potassium-tert.-butoxid by dehydrohalogenation / prototropic rearrangement to phenoxyvinyl sulfanes, the E,E-bis(1-phenoxy-propen-2-yl)-sulfanes 3. Sulfanes 3 are of special interest as a model for unsaturated macrocycles B derivated from dithiacrown ethers A. The configuration was assigned using 1H-n.m.r.- and 13C-n.m.r.-spectroscopy. The molecular structure was determinded by X-ray diffraction techniques. Rearrangement of sulfur-substituted allyl ethers 2 to the propenyl isomers 3a proceeds in a stereospecific manner as for common allyl ethers described in the literature.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19933350803
