ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The regioselectivity of transannular O-heterocyclization of cycloocta-1,5-diene (1) with phenylsulfenyl chloride and methanol or water, respectively, is determined by the oxy-component which acts as nucleophilic partner in the electrophilic three component reaction. The thermodynamically more stable endo, endo-2,6-bis(phenylsulfenyl)-9-oxabicyclo[3.3.1]nonane (2) is formed almost exclusively in methanol while the isomeric 9-oxabicyclo[4.2.1]nonane (3) is favored under kinetic control in the presence of water. The oxidation of 2 or 3 yields the bissulfones 4 and 5, respectively.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19983400508
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