Work

Synthesis of α-Nitro Carbonyls via Nitrations in Flow

Year: 2016

Type: article

Abstract: Reported is a safe, rapid method for the synthesis of α-nitro esters via the trapping of nitronium ions. The two-stage nitration and subsequent deacetylation of readily available 1,3-dicarbonyl compounds was achieved using a biphasic semicontinuous approach. α-Nitro esters and amides were obtained in good overall yields (53-84%). Some of the α-nitro-1,3-dicarbonyl intermediates exhibit enhanced reactivity and undergo an acid-catalyzed Nef-type reaction to α-oxo-carbonyls.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.6b01634

Authors: Anna Chentsova, Dmitry B. Ushakov, Peter H. Seeberger, Kerry Gilmore

Institutions: Max Planck Institute of Colloids and Interfaces, Freie Universität Berlin

Language: English

Topic: Innovative Microfluidic and Catalytic Techniques Innovation

Subfield: Biomedical Engineering

Field: Engineering

Domain: Physical Sciences

Open Access status: green

Funder: Max-Planck-Gesellschaft

OpenAlex ID: W2516576736

FWCI: 1.125

Cites: 66

Cited by: 12

Related to: 10