Brominating and oxidizing agent and method of using same

Details Brominating and oxidizing agent and method of using same Brominating and oxidizing agent and method of using same

1975-06-16

1977-02-22

Rush, Raymond V.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603971, 2603972, 2603974, 260586R, 260590R, 260593R, 260635H, 260659R, C07D26322

Patent

active

040091783

ABSTRACT:
There is provided a brominating and oxidizing agent of the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different, represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.22 straight or branched alkyl group, a phenyl group, and a substituted phenyl group whose substituents are selected from the group consisting of a methoxy group, a nitro group, a cyano group, a halogen atom (Br, Cl, I), a C.sub.1 -C.sub.2 dialkylamino group, a C.sub.1 -C.sub.2 dialkylaminomethyl group, a C.sub.1 -C.sub.2 dialkylaminoethyl group, a C.sub.1 -C.sub.2 dialkylammoniummethyl group, a C.sub.1 -C.sub.2 dialkylammoniumethyl group, a C.sub.1 -C.sub.2 trialkylammoniummethyl group, a C.sub.1 -C.sub.2 trialkylammoniumethyl group, a COOR.sub.5 group, and a CON(R.sub.5).sub.2 group, wherein R.sub.5 represents a C.sub.1 -C.sub.8 straight or branched alkyl group.
The compounds falling within formula (I) find wide application as brominating and oxidizing agents in a number of organic reactions in which the prior art compound, N-bromosuccinimide has been employed to date. In comparison to N-bromosuccinimide, the compounds of the instant invention are characterized as being extremely stable to degradation and less polar with respect to their N-Br bond than N-bromosuccinimide such that promotion of "radical" bromine release is achieved with minimal positive bromine release.

REFERENCES:
patent: 3465674 (1969-09-01), Walles et al.
patent: 3591601 (1971-07-01), Walles
patent: 3850920 (1974-11-01), Walles
patent: 3931213 (1976-01-01), Kaminski et al.

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