Stereocontrolled double ring expansion of fused allylidenecyclopropanes. A novel route to hydroazulenes and other fused bicyclic systems

Autor:	Craig A. Shook, Manchao Xiao, James P. Sherbine, Theodore Cohen, Matthew L. Romberger, S.-H. Jung, Fu Tyan Lin, Birong Zhang
Rok vydání:	1993
Předmět:	chemistry.chemical_classification Ketone Flash vacuum pyrolysis Trimethylsilyl Bicyclic molecule Regioselectivity General Chemistry Biochemistry Catalysis chemistry.chemical_compound Colloid and Surface Chemistry chemistry Polymer chemistry Epimer Enone Peterson olefination
Zdroj:	Journal of the American Chemical Society. 115:10754-10773
ISSN:	1520-5126 0002-7863
Popis:	A variety of 1-(phenylthio)-1-(trimethylsilyl)cyclopropanes, fused to five-, six-, and seven-membered rings have been prepared by several procedures and reductively lithiated by means of aromatic radical anions. The resulting 1-lithio-1-(trimethylsilyl)cyclopropanes have been treated in most cases with α,β-unsaturated aldehydes, followed by potassium tert-butoxide to yield allylidenecyclopropanes. The latter, upon thermal rearrangement either in a sealed tube or in a flash vacuum pyrolysis apparatus, undergo a double ring expansion to cyclopentenocyclohexenes, -cycloheptenes (hydroazulenes), or -cyclooctenes
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e239a5470f21c85492dc0d9d2e0906d7 https://doi.org/10.1021/ja00076a037 Zobrazit plný text záznamu