7789-90-4Relevant academic research and scientific papers
Synthesis and reactivity of novel α,α,β- and α,α,δ-trichlorinated imines
D'Hooghe, Matthias,De Meulenaer, Bruno,De Kimpe, Norbert
scheme or table, p. 2437 - 2442 (2009/04/08)
A variety of different N-(2,2,3-trichloropropylidene)amines, N-(2,2,3-trichlorobutylidene)amines, and N-(2,2,5-trichloropentylidene)amines were synthesized for the first time, and their reactivity with regard to hydride reagents was investigated. In this way, N-(2,2,5-trichloropentylidene)amines were evaluated as substrates for the synthesis of piperidines, and N-(2,2,3-trichloropropylidene)amines and N-(2,2,3-trichlorobutylidene)amines were reduced efficiently into the corresponding novel β,β,γ- trichloroamines by means of sodium cyanoborohydride in methanol in the presence of acetic acid. Furthermore, N-(2,2,3-trichloropropylidene)amines were transformed into 2-(chloromethyl)aziridines by lithium aluminium hydride in Et2O, and N-(2,2,5-trichloropentylidene)acetamide was used for the first time as a suitable substrate for the addition of oxygen, nitrogen, and sulfur nucleophiles in good yields. Georg Thieme Verlag Stuttgart.
