
TY  - JOUR
A1  - Baker, MV 
A1  - Ghitgas, C 
A1  - Haynes, RK 
A1  - Hilliker, AE 
A1  - Lynch, GJ 
A1  - Sherwood, GV 
A1  - Yeo, H 
T1  - The preparation of ethyl and isopropyl dienol ethers and dienol pivalate esters from Hagemann's ester and its t-butyl analogue, and the reactions of the derived ester dienolates with electrophiles
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1984
VL  - 37
IS  - 10
SP  - 2037
EP  - 2058
KW  - 
UR  - https://doi.org/10.1071/CH9842037 
N2  - The preparation of ethyl 4-ethoxy-2-methylcyclohexa-1,3-diene-1-carboxyate, 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-butyI 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 diisopropyl- amide in tetrahydrofuran at -78&quot; to give the corresponding ester dienolates, which react regio- specifically with a number of electrophiles, either a or y 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 derivatives substituted exclusively at C1. 
ER  -

