ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of Triafulvene-Precursors from Trisubstituted CyclopropanesTrisubstituted cyclopropanes 5a-f are prepared by carbene addition to the appropriate olefins. While 5a (Y = OAc) and 5c (Y = Cl) rearrange in the presence of BuLi, 5d (Y = SPh) is stable enough to allow the envisaged sequence for triafulvene (Scheme 2) : halogen-Li exchange, followed by methylation of 6d, gives 7d in a 93% yield; after base-induced elimination of HBr from 7d, the key precursor 1-methylene-2-(phenylthio)cyclopropane (9, 70% yield) is isolated. Compound 9 is transformed into the corresponding sulfoxide 10 (83%), sulfone 11 (80%), and sulfonium fluoroborate 12 (95% yield) by subsequent oxidation and methylation, respectively. Some 1H-NMR results of cyclopropanes 5a-f and 7d as well as of methylidene-cyclopropanes 9-11 are discussed.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19880710820