91358-63-3Relevant academic research and scientific papers
THE PREPARATION AND REACTIONS OF DIENOL ETHER AND DIENOL ESTER DERIVATIVES OF HAGEMANN'S ESTER AND ITS t-BUTYL ANALOGUE
Baker, Murray V.,Ghitgas, Christine,Haynes, Richard K.,Hilliker, Audrey E.
, p. 1625 - 1628 (2007/10/02)
The efficient conversion of Hagemann's ester and its t-butyl analogue into dienol ethers and dienol esters, and reactions of the derived dienolates with electrophiles is described.
The Preparation of Ethyl and Isopropyl Dienol Ethers and Dienol Pivalate Esters from Hagemann's Ester and its t-Butyl Analouge, and the Reactions of the Derived Ester Dienolates with Electrophiles
Baker, Murray V.,Ghitgas, Christine,Haynes, Richard K.,Hilliker, Audrey E.,Lynch, Gregory J.,et al.
, p. 2037 - 2058 (2007/10/02)
The preparation of ethyl 4-ethoxy-2-methylcyclohexa-1,3-diene-1-carboxylate, ethyl 4-isopropoxy-2-methylcyclohexa-1,3-diene-1-carboxylate, t-butyl 4-isopropoxy-2-methylcyclohexa-1,3-diene-1-carboxylate, ethyl 4-(t-butylcarbonyloxy)-2-methylcyclohexa-1,3-diene-1-carboxylate, and t-butyl 4-(t-butylcarbonyloxy)-2-methylcyclohexa-1,3-diene-1-carboxylate from Hagemann's ester and its t-butyl analogue in the presence of diethyl or diisopropyl sulfates and sodium hydride in dimethyl sulfoxide, or pivaloyl chloride and N,N,N',N'-tetramethylethylenediamine in tetrahydrofuran is described.The foregoing dienol ethers and esters are smoothly deprotonated by lithium diisopropylamide in tetrahydrofuran at -78 deg C to give corresponding ester dienolates, which react regiospecifically with a number of electrophiles, either α or γ to the alkoxycarbonyl group of the dienol ether or ester.A number of the products, which are generally obtained in good yields, have been hydrolysed to Hagemann's ester dirvatives substituted exclusively at C 1.
