Electrochemical additions to alkenes
AssigneeNational Research Development Corporation
InventorsAlan Bewick, David E. Coe, John M. Mellor, David J. Walton
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Abstract
Organic compounds having vicinal functional groups, such as amidothioethers and esterthioethers, are prepared by electrochemically oxidizing an organic disulphide, an organic diselenide, a hexasubstituted organic disilane or a tetrasubstituted organic hydrazine in the presence of an alkene and an organic nucleophile.
Claims8
A process for the preparation of an organic compound having vicinal functional groups which process comprises electrochemically oxidizing (a) an organic disulphide, (b) an organic diselenide, (c) a hexasubstituted organic disilane or (d) a tetrasubstituted organic hydrazine of the formula:
- Y--Y'
- wherein:
- (a) Y and Y' independently represent RS--;
- (b) Y and Y' independently represent RSe--;
- (c) Y and Y' independently represent ##STR10## or (d) Y and y' independently represent ##STR11## and each R independently represents an alkyl, alk-2 to 6-enyl, phenylalkyl, phenyl or heterocyclic group optionally substituted by one or more functional groups which are inert under the process conditions, in the presence of:
- (1) an alkene of the formula:
- ##STR12## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently represent hydrogen alkyl, phenylalkyl, phenyl, carboxy, alkoxycarbonyl, phenylalkoxycarbonyl or phenoxycarbonyl or R.sub.1 and R.sub.3 together represent alkylene optionally substituted in the hydrocarbon chain by alkylimino, phenylalkylimino, phenylimino, oxygen or sulfur and wherein said hydrocarbon groups and moieties are optionally substituted by one or more functional groups which are inert under the process conditions and
- (2) an organic nucleophile to yeild an organic compound of the formula:
- ##STR13## wherein:
- Y, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined above, and
- Nu is the functional group derived from the nucleophile.
A process for preparing amidothioethers of the formula:
- ##STR19## wherein:
- R represents C.sub.1 -C.sub.4 alkyl, phenyl C.sub.1 -C.sub.4 alkyl or phenyl,
- R.sub.1 ', R.sub.2 ', R.sub.3 ', and R.sub.4 ' independently represent hydrogen or C.sub.1 -C.sub.6 alkyl or R.sub.1 ' and R.sub.2 ' together C.sub.2 -C.sub.6 alkylene;
- and
- R.sub.5 represents C.sub.1 -C.sub.4 alkyl, said process comprising electrochemically oxidizing an organic disulphide of the formula:
- RSSR
- wherein R is as defined above, in the presence of:
- (1) an alkene of the formula ##STR20## wherein R.sub.1 ', R.sub.2 ', R.sub.3 ' and R.sub.4 ' are as defined above, and
- (2) a nitrile of the formula
- R.sub.5 CN
- wherein R.sub.5 is as defined above, and water is added to the anolyte after termination of the electrolysis.
Dependencies are inferred from the claim text.