Synthesis of α-Bromoketones

Abstract

A new synthesis of a-bromoaldehydes based upon the bromination of enol acetates of aldehydes was described in a previous paper.2 The

Conformational analysis of 2-halocyclohexanones: an NMR, theoretical and solvation study

“…17 ∆E = E eq Ϫ E ax (2) volume V M of 132.12 for the bromo compound was obtained using the literature value of the pure liquid density. 21 This is incompatible with the other values in Table 4 obtained from MODELS using additive atomic volumes. These MODELS values are in complete agreement with the corresponding values for the cyclohexyl halides obtained directly from the observed values of the densities.…”

Enantioselective electrochemical oxidation of enol acetates using a chiral supporting electrolyte

“…All of the starting compounds and the products were characterized by a variety of spectroscopic methods (NMR: JNM-EX-400 from JEOL Co., GC-MASS: QP2000A from Shimadzu Co., and IR: IR-810 from Jasco Co., Japan) and elemental analysis (CHN CODER MT-6 from Yanaco Co., Japan). 15,16 Into isopropenyl acetate (200 mL) containing ptoluenesulfonic acid monohydrate (1 mmol) was added an appropriate ketone (50 mmol), and the mixture was heated to remove acetone continuously according to the reported procedure. 15,16 After the reaction, the mixture was poured into a two-layer solution of aqueous saturated NaHCO 3 and ethyl ether and extracted with 3 × 100 mL.…”

“…15,16 Into isopropenyl acetate (200 mL) containing ptoluenesulfonic acid monohydrate (1 mmol) was added an appropriate ketone (50 mmol), and the mixture was heated to remove acetone continuously according to the reported procedure. 15,16 After the reaction, the mixture was poured into a two-layer solution of aqueous saturated NaHCO 3 and ethyl ether and extracted with 3 × 100 mL. of ethyl ether with vigorous stirring.…”

Derivatization of keto fatty acids: II. synthesis of long‐chain enolacetates

“…Another type of vinyl structure can be formed from keto fatty acids in which the keto group forms carbanions or enolate ions which can be trapped in the acylated or metalated form. Bedoukian (7) has developed an easy and general method for the preparation of enolacetates, using acetic anhydride and p-TSA. It was apparent from a survey of the literature that a number of methods are available for the synthesis of enolacetates (4)(5)(6).…”