Cathy Einhorn

Selective allylation of carbonyl compounds in aqueous media

Abstract The use of aqueous neutral media leads to excellent yields of homoallylic alcohols from reaction sof allyl halides with carbonyl compounds in the presence of tin or zinc. The stereochemical course and range of application of this reaction have been investigated.

Organic sonochenistry : A new interpretation and its consequences

Abstract A rational approach of sonochemical reactions is proposed on the basis of their mechanisms. It appears that reactions which can be modified in their rate or nature of products, by ultrasound irradiation, correspond to those which proceed, at least in part, through radical intermediates.

New aerobic oxidation of benzylic compounds: efficient catalysis by N-hydroxy-3,4,5,6-tetraphenylphthalimide (NHTPPI)/CuCl under mild conditions and low catalyst loadingElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b4/b403004d/

Efficient aerobic oxidation of benzylic compounds using NHTPPI, a new NHPI analogue, as a key catalyst combined with CuCl, have been achieved under mild conditions and using as little as 1 mol% catalyst.

A Convenient Method for the Preparation of N-Methoxyamides

Abstract A variety of N-methoxyamides is easily prepared from carboxylic acids and N,O-dimethylhydroxylamine hydrochloride in the presence of triphenylphosphine and carbon tetrabromide.

Organic sonochemistry - some illustrative examples of a new fundamental approach

The sonochemical behaviour of several organic reactions, selected according to their mechanisms, has been examined. Their experimental evolution follows the prediction developped previously, that sonication promotes reactions proceeding through radical pathways.

A versatile and regiospecific synthesis of functionalized 1,3-diarylisobenzofurans.

A convenient, versatile, and regiospecific synthesis of functionalized 1,3-diarylisobenzofurans has been developed. It involves chemoselective addition of arylmagnesium reagents to the aldehyde function of o-aroylbenzaldehydes, themselves readily obtained by lead tetraacetate oxidation of N-aroylhydrazones of salicylaldehydes. Various functional groups, including nitro, iodo, or ester functionalities, have thus been positioned with complete regiospecificity on the 1,3-diphenylisobenzofuran backbone.

Electrocatalytic oxidation of alcohols using substituted N-hydroxyphthalimides as catalysts

The electrocatalytic oxidation of several alcohols was performed using a new series of substituted N-hydroxyphthalimides as catalysts. The substitution in the N-hydroxyphthalimide structure by electron withdrawing or donor substituents has a beneficial effect on the efficiency of the electrocatalytic oxidation of borneol, used as a model, although the progressive degradation of the catalysts during preparative electrolyses is observed. In the case of lowest activated alcohols such as 2-octanol the use of the regular structure allows the best chemical yield in the corresponding carbonyl compounds to be obtained. Moreover, primary alcohol oxidation under anaerobic conditions leads to the corresponding aldehyde exclusively, whereas in the presence of molecular oxygen a mixture of the corresponding aldehyde and carboxylic acid is obtained.

Nucleophilic properties of butyllithium versus free carboxylic acids

Abstract In opposition to the generally accepted idea, butyl lithium is not only a deprotonating agent for free carboxylic acids, but can also act as a nucleophile on the carbon oxygen double bond.

SYNTHESIS AND RESOLUTION OF A CHIRAL ANALOGUE OF 2,2,6,6-TETRAMETHYLPIPERIDINE AND OF ITS CORRESPONDING NITROXIDE

Abstract The novel C2 symmetric chiral amine trans-2,6-dimethyl-2,6-diphenylpiperidine has been synthesized via two successive nitrone nucleophilic addition-oxidation sequences, followed by reduction of the intermediate nitroxide. Pure enantiomers have been obtained via resolution with mandelic acid.

Ultrasound in organic synthesis 15. Radical cyclisation of o-allyl benzamides via the sonochemically generated radical anions

Abstract By reaction with lithium metal in THF under sonochemical activation, o-allyl tertiary benzamides are easily cyclised to 2-methyl-indanone. Yields strongly depend on the substitution pattern of the nitrogen atom.