72518-46-8Relevant academic research and scientific papers
Rearrangements of Cycloalkenyl Aryl Ethers
T?rincsi, Mercedesz,Nagy, Melinda,Bihari, Tamás,Stirling, András,Kolonits, Pál,Novak, Lajos
, (2016/05/24)
Rearrangement reactions of cycloalkenyl phenol and naphthyl ethers and the acid-catalyzed cyclization of the resulting product were investigated. Claisen rearrangement afforded 2-substituted phenol and naphthol derivatives. Combined Claisen and Cope rearrangement resulted in the formation of 4-substituted phenol and naphthol derivatives. In the case of cycloocthylphenyl ether the consecutive Claisen and Cope rearrangements were followed by an alkyl migration. The mechanism of this novel rearrangement reaction is also discussed.
SYNTHESIS AND STEREOCHEMISTRY OF ACIDOLYLSIS OF SOME CYCLOHEPT-2-ENYLSTANNANES AND -SILANES
Kitching, William,Penman, Kerry G.,Laycock, Bronwyn,Maynard, Ian
, p. 3819 - 3832 (2007/10/02)
A range of methyl-substituted cyclohept-2-enyltrimethylstannanes and trimethylsilanes have been synthesized and characterised by 1H, 13C and 119Sn (or 29Si) nmr spectroscopy.Key conformational characteristics of some of these compounds are discussed.Acidolysis of these stannanes and silanes (with CF3COOD) proceeds cleanly to provide the 2H-substituted methylcycloheptene resulting from allylic rearrangement i.e. regiospecific γ-attack by the electrophile (SE').Detailedexamination of the 2H nmr spectra of the methylcycloheptenes establishes a highly preferred, if not specific, γ-anti mode of electrophile delivery.Thus, this γ-anti-SE' process may from the basis of synthetically useful applications in what is sometimes an awkward ring system for functionalization.
