SYNTHETIC EXPLOITATION OF HALOGENATED ALKENES CONTAINING ELECTRON-WITHDRAWING GROUP (EWG): ACCESS TO VALUABLE 2,4-DINITROTHIOPHENES VIA RING-CLOSING AND RING-OPENING/RING-CLOSING PROTOCOLS

With the goal of their exploitation for the synthesis of highly functionalized 2,4-dinitrothiophenes, 2-(2,3-dichloro-1,3-dinitroallylidene)-1,3-dithiolane (2), derived from the initial ring-closing of polyhalogenated nitrobutadienic building blocks with 1,2-ethanedithiol, were reacted with secondary amines. After protic work up, highly functionalized 2,4-dinitrothiophenes have been accomplished via ring-opening/ring-closing protocols

Synthetic exploitation of halogenated alkenes containing an electron-withdrawing group: synthesis of alpha-chlorohydrazones and ketene aminals by regiospecific reactions of in situ generated imide chlorides

A concise approach for the construction of ketene aminals and alpha-chlorohydrazones has been developed. It involves reactions of the regiodefined gem-dihalo nitrovinyl compound of in situ generated imide chlorides in different media with primary arylamines being dependent on the aryl groups. A range of ketene aminals and alpha-chlorohydrazones are obtained in good to high yields. In addition, alpha-aminohydrazones are prepared by using alpha-chlorohydrazones as the precursors. (C) 2014 Elsevier Ltd. All rights reserved

Synthetic exploitation of halogenated alkenes containing EWG: benzotriazole-mediated synthesis of benzoazetines and thermal transformations

The series of stable benzoazetine derivatives (5a-d) based on nitrovinyl moieties have been synthesized via transamination of bisbenzotriazolyl derivatives (2a-c). Four new heptatomic aromatic cycloheterocumulenes (azacyclohepta-1,2,4,6-tetraene) occurring at the stage of the film-forming process by TVE have been obtained by rearrangement of benzoazetines. The highly strained products were characterized by IR spectroscopy

REACTIVITY STUDY OF 2,4-DINITROBUTA-1,3-DIENES TOWARDS MONO-, POLY-, AND PERSULFANYL CONJUGATED DIENES BY REGIOSPECIFIC VINYL GROUP ACTIVATION

Polyhalogenated nitrobuta-1,3-dienes are unique reagents in organic synthesis and have been employed in several well-known and recently developed areas of application. This study describes the scope and application of 1,1,3,4-tetrachloro-2,4-dinitrobuta-1,3-diene in organic synthesis as well as methods for the preparation of poly-and perfunctionalized 2,4-initrobuta-1,3-dienes, and characterization of all obtained compounds