ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The two-step alkylation of phenyl prop-2-enyl sulfone (1) with protected ω-bromoalkanols and 1-iodoalkanes (→3; see Scheme 1) followed by a Pd-catalyzed desulfonylation with LiBH4 affords a 96:4 mixture of vinylbranched, protected alcohols and corresponding ethylidene-branched isomers (see Scheme 2; 4 and 5, respectively). By utilizing the large difference in reactivity of mono- and trisubstituted C=C bonds towards singlet oxygen, the ethylidene derivatives are easily removed from the mixture by photo-oxygenation. The vinyl-branched compounds are inert to this reaction and can be conveniently isolated in highly pure form (99.5%) and ca. 45% overall yield.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19940770510
Permalink