title: Powerful Bispyridinylidene Organic Reducing Agents with Iminophosphorano π-Donor Substituents.
abstract: Four members of a new family of powerful bispyridinylidene organic reducing agents have been prepared, which exploit iminophosphorano (-N=PR3; R = Ph, Cy) π-donor substituents. Electrochemical studies show exceptionally high oxidation potentials, ranging from 1.30 to 1.51 V versus SCE. These new reductants were shown to effectively convert 1-bromonaphthalene to naphthalene under mild reaction conditions. From the redox potentials, substituent constants (σp(+)) for the iminophosphorano groups Ph3P=N- (-1.82) and Cy3P=N- (-2.21) were determined, demonstrating their superior π-donating properties compared to traditional amino substituents.
authors: Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3 (Canada).
authors: Samuel S
authors: SS
authors: Hanson
authors: Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3 (Canada).
authors: Nicholas A
authors: NA
authors: Richard
authors: Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3 (Canada). cadyker@unb.ca.
authors: C Adam
authors: CA
authors: Dyker
keywords: electron transfer; iminophosphorane; organic reductant; reduction; substituent effects