Shell Oil Comapny

Shell Internationale Research Maatschappij, B.v.

Ronald F Mason

Derek A Wood

Barry R Devlin

Paul H Briner

Royston H Davis

Roger A Sheldon

Gary Scholes

Peter Been

Herbert P Rosinger

Jan W Van Reijendam

Margaretha J De Nie-Sarink

The novel ester, N-benzylazetidine-3-carboxylic acid methyl ester and its use in the preparation of the corresponding free acid by a process which comprises reacting N-benzyl-3-cyanozetidine with methanol and hydrolyzing the resulting methyl ester with hot water.

Azetidine-3-carboxylic acid derivatives

2-Benzyl-7,7-dimethyl-6,8-dioxa-2-aza-spiro[3,5]nonane of the formula ##STR1## and a process for the preparation of that compound, which compound is useful as an intermediate in the preparation of 3-carboxy azetidine.

Azetidine derivative

The invention provides a process for preparing azetidine-3-carboxylic acid or salts thereof; useful as chemical hybridizing agents, which comprises treating a compound of the formula ##STR1## wherein R represents a hydrogen atom or a group of formula R.sup.1 R.sup.2 CH-- wherein R.sup.1 and R.sup.2 are independently selected from hydrogen, alkyl or optionally substituted phenyl moieties, with nitric acid and subjecting the resulting initial product to acid conditions to produce an acid-addition salt of azetidine-3-carboxylic acid, and thereafter, if desired, converting the acid-addition salt to the free acid or another salt of the acid, 1-nitrosoazetidine-3,3-dicarboxylic acid, 1-nitrosoazetidine-3-carboxylic acid and salts thereof being intermediates in the process.

Process for preparing azetidine derivatives and intermediates thereof

Substituted azetidine derivatives of formula ##STR1## in which R represents chlorine, bromine, hydroxy or alkanoyloxy of up to 6 carbon atoms, processes for their preparation and their use as intermediates for the preparation of azetidine-3-carboxylic acid.

N-benzyl,3-hydroxymethyl and 3-alkanoyloxymethyl azetidine derivatives

Novel compounds of the general formula ##STR1## in which X is hydrogen or chlorine, and each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently is hydrogen, methyl or ethyl, are useful intermediates in the preparation of the corresponding phenols. They may be prepared by treating a compound of the formula ##STR2## in which Hal is chlorine or fluorine, with a compound of the formula

Novel substituted phenyl ethers, process for their preparation, and

This invention relates to the preparation of cyclopropane carboxylic acid ester derivatives, which are useful as pesticides. There is provided a process for preparing a 1:1 mixture of 1R cis S- and 1S cis R- isomers substantially free of 1S cis S- and 1R cis R- isomers of a compound of formula: ##STR1## wherein R.sup.1 and R.sup.2 are each independently selected from chlorine, bromine and methyl, which process comprises dissolving a mixture of 1S cis S- and 1R cis R- isomers of the compound of formula I, alone or in the presence of 1R cis S- and 1S cis R-isomers, in organic amine base containing from 5 to 7 carbon atoms and being a secondary amine containing two branched alkyl groups or a tertiary amine, and crystallizing out from the resulting solution of cis - isomers of formula I in the organic amine base a 1:1 mixture of the 1R cis S- and 1S cis R- isomers substantially free of 1S cis S- and 1R cis R- isomers. The process of the invention yields a product which contains substantially twice as much of the most active isomer of the compound of formula I as a racemic mixture of all four cis - isomers, and is a readily effected process which does not involve any asymmetric synthesis or optical resolution steps.

Process for preparing cyclopropane carboxylic acid ester derivatives

Mixtures of the geometric isomeric forms of 3-azabicyclo-(3.1.0)hexane-2-carbonitrile are resolved by selective extraction of a mixture of their benzenesulfonic acid salts or their toluenesulfonic acid salts.

Separation of isomers

Certain 3-azabicyclo(3.1.0)hexane-2-carbonitriles, and a method for their preparation.

3-Azabicyclo(3.1.0)hexane-2-carbonitrile

3-Azabicyclo(3.1.0)hexan-4-one-2-carbonitriles, and a method for their synthesis.

3-Azabicyclo(3.1.0)hexan-4-one-2-carbonitrile

Certain carboxylic acid esters also containing a cyano group are prepared by reacting an acid halide, an aldehyde and a water-soluble cyanide in the presence of a water immiscible aprotic solvent and preferably a phase-transfer catalyst.

Preparation of esters

Alkyl esters of 3-cyano-3-(3-phenoxyphenyl)-2-ketopropionic acid, useful as precursors for the preparation of insecticidal esters of 3-phenoxy-.alpha.-cyanobenzyl alcohol.

Precursors for insecticides

3-PHENOXYBENZYL BROMIDE IS PREPARED BY TREATING 3-PHENOXYTOLUENE WITH BROMINE IN THE PRESENCE OF ULTRA-VIOLET RADIATION, AT A TEMPERATURE IN THE RANGE OF FROM 180.degree. C to 250.degree. C.

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Ashford, United Kingdom

Ronald F Mason