Unsymmetrical Tetraalkylmethanes. III.¹ Syntheses from 3-Ethyl-3-methylglutaric Acid

Abstract

Ill 359 Small amounts of dialkylphosphines are formed.

Mass spectra of certain cycloalkylacetates and of related unsaturated esters

“…A reasonable mechanism for this fragmentation is shown in Scheme III, wherein the initial step is loss of an electron from the ring bond between the substituents to give the radical ion 21. Fragmentation of this ion as shown could give the resonance-stabilized ion (22). Although stabilization of this ion is decreased by the proximity of the Scheme III positive charge to the ester group, its energy would be lowered significantly.…”

“…Dimethyl /3-Ethyl-d-methyladipate.-/3-Ethyl-d-methylglutaric acid was prepared according to Rabjohn and Farmer,21 and converted to 3-ethyl-3-methyl-4-methoxycarbonylbutanoyl chloride by way of the methyl half-ester, as has also been reported. 22 The above-described ester acid chloride was treated in 3-g lots with 1.7 g of diazomethane in 150 ml of ether, at a temperature of 5-10°. After the reaction mixture had stood overnight solvent was removed at reduced pressure and the residual diazo ketone was dissolved in 10 ml of absolute methanol.…”