Alkylations employing in situ generation of diazoalkane alkylati

Details Alkylations employing in situ generation of diazoalkane alkylati Alkylations employing in situ generation of diazoalkane alkylati

1974-01-17

1976-06-15

Raymond, Richard L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260468R, 260469, 260471R, 260478, 260563R, 260568, 260583R, 260609R, 260611R, 260611A, 260612D, 260614R, 260684, 260692, C07B 2700

Patent

active

039636984

ABSTRACT:
Alkylation processes wherein diazoalkane alkylation reagents are generated in situ and utilized to alkylate substrates are disclosed. These processes utilize the relatively slow base-catalyzed decomposition of an N-alkyl, N-nitrosourea to produce a corresponding diazoalkane alkylation reagent, followed by the much faster reaction between the alkylation reagent and the substrate to be alkylated. Generically, suitable ureas can be represented by the structural formula, ##EQU1## wherein R represents the alkyl moiety to be added to the substrate; R can be alkyl, cycloalkyl, heteroalkyl, aralkyl or heterocyclic.
This process is useful in producing alkylated products without the concomitant disadvantage of building up significant amounts of diazoalkane alkylation reagents during the course of the reaction, many of which have deleterious properties.

REFERENCES:
theilheimer; W., (1966), Synthetic Methods of Organic Chemistry, vol. 20, Pub. by S. Karger, N.Y., p. 475 cited.
Vogel; A. I., Practical Organic Chemistry, 3rd Edtn., Pub. by John Wiley of N.Y., (1965), pp. 968 and 973 relied on.

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