Concepedia

Convenient Access to Primary Amines by Employing the Barbier-Type Reaction of <i>N</i>-(Trimethylsilyl)imines Derived from Aromatic and Aliphatic Aldehydes

Ferenc Gyenes, Kathryn E. Bergmann, John T. Welch

The Journal of Organic Chemistry · 1998 · 33 citations · 26 references

DOI

Concepts

Abstract

A new versatile preparation of primary amines via benzylation of aromatic and aliphatic aldimines is described. Sonochemical and traditional methods for generation of the reactive intermediates are compared and contrasted. Competitive reactions were analyzed via free energy relationships to support the proposed alkylative mechanism.

References

26

Preparation of primary amines and 2-azetidinones via N-(trimethylsilyl)imines

David J. Hart, Kenichi Kanai, Dudley G. Thomas et al. · The Journal of Organic Chemistry · 1983 · 183 citations

, , +6

.eta.3 and .eta.6 Bridging cations in the N,N,N',N'',N''-pentamethyldiethylenetriamine-solvated complexes of benzylpotassium and benzylrubidium: an x-ray, NMR, and MO study

Daniele Hoffmann, Walter Bauer, Frank Hampel et al. · Journal of the American Chemical Society · 1994 · 131 citations · Full text

, , +6

Carbohydrates as chiral templates: diastereoselective synthesis of N-glycosyl-N-homoallylamines and .beta.-amino acids from imines

Sabine Laschat, Horst Kunz · The Journal of Organic Chemistry · 1991 · 110 citations

, , +8

Diastereofacial selectivity in the reaction of allylic organometallic compounds with imines. Stereoelectronic effect of imine group

Yoshinori Yamamoto, Toshiaki Komatsu, Kazuhiro Maruyama · The Journal of Organic Chemistry · 1985 · 101 citations

, , +5

.alpha.-Amino acids as chiral educts for asymmetric products. Alkylation of N-phenylfluorenyl .alpha.-amino ketones. Synthesis of optically pure .alpha.-alkyl carboxylic acids

William D. Lubell, Henry Rapoport · Journal of the American Chemical Society · 1988 · 72 citations

, , +14