title: Substituent controlled reactivity switch: selective synthesis of α-diazoalkylphosphonates or vinylphosphonates via nucleophilic substitution of alkyl bromides with Bestmann-Ohira reagent.
abstract: We report a substituent controlled nucleophilic displacement of alkyl bromides with Bestmann-Ohira reagent yielding either dimethyl diazoalkylphosphonates or (E)-vinylphosphonates. The dimethyl diazoalkylphosphonates could be readily converted into corresponding (E)-vinylphosphonates in the presence of Cu following nitrogen elimination in quantitative yields.
authors.affiliation: Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram extension, Sitapur Road, P.O. Box 173, Lucknow 226031, India. namrataiit@gmail.com namrata.rastogi@cdri.res.in.
authors.forename: Mukund M D
authors.initials: MM
authors.lastname: Pramanik
authors.forename: Atul Kumar
authors.initials: AK
authors.lastname: Chaturvedi
authors.forename: Namrata
authors.initials: N
authors.lastname: Rastogi
mesh_terms: D000478:Alkylation; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001965:Bromides / Q000737:chemistry*; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D007202:Indicators and Reagents; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D011720:Pyrazoles / Q000138:chemical synthesis
chemical_list: D001391:Azo Compounds; D001965:Bromides; D007202:Indicators and Reagents; D063065:Organophosphonates; D011720:Pyrazoles; D003300:Copper