Romuald Bartnik

Synthese de fluoro-3 azacyclanes : action de l'acide fluorhydriqiue sur les aza-1 bicyclo [n.1.0] alcanes

Abstract The addition of liquid hydrogen fluoride or Olahs reagent (pyridin-10 HF) to 1-aza bicyclo [n.1.0] alkanes leads to the formation of 3-fluoro 1-aza heterocyclic compounds. Isomeric 3-fluoro azetidines, 3-fluoro piperidines and a 3-fluoro azepine have been prepared by this procedure.

A new synthesis of enaminoketones

Abstract A new and efficient synthesis of enaminoketones is described. E,Z β-chloroacroleine derivatives react with secondary amines to produce enaminoketones. The reaction was essentially studied with β-trifluoromethylacroleines.

Synthese photochimique d'aza-1 bicyclobutanes

Abstract Aza-1 bicyclobutanes 2 are readily obtained by photolysis of carbamates 1 . 1 are easily synthetised from 3 .

Alkylation et silylation de 2h-azirines

Resume Alkylation and silylation of 2H-azitines are reported. Methylation of lithiated azirines is always observed at the carbon atom. N- or C-silytated azirines can be obtained depending on the silyl reagents or substrates.

New Method for the Generation and Trapping of 1-Azabicyclo[1.1.0]butane. Application to the Synthesis of 1,3-Dinitroazetidine

Abstract 1-Azabicyclo[1.1.0]butane (1) has been prepared via a two-step, one-pot procedure that involves (i) reaction of a heptane solution of allylamine with N-chlorosuccinimide at 0 °C followed by (ii) codistillation of the product from basic solution along with heptane-octane. Compound 1 thereby obtained was extracted from the distillate by using cold aqueous NaNO2. Subsequent treatment of the aqueous extract with cold concentrated aqueous HCl afforded N-nitroso-3-nitro-azetidine (4) in 5.5% yield. Oxidation of 4 with 100% HNO3 produced N,3-dinitroazetidine (5, 90%). This reaction sequence constitutes a formal synthesis of 1,3,3-trinitroazetidine (TNAZ), an important energetic material.

A New Route to 3-Phosphonylpyrazoles

The regioselective synthesis of 3-diethoxyphosphonopyrazoles has been accomplished through the addition of aryl or alkyl hydrazines to (3-ethoxyacryloyl)phosphonic acid diethyl ester. An example of hydrolysis of the pyrazolephosphonic ester to the corresponding acid is described.

A Convenient One-Pot Synthesis of β -(Trifluoromethyl)allylaminophosphonic and Benzylaminophosphonic Acids

The reductive condensation of aminoalkylphosphonic acids with β -chloro- or β -ethylthio-(β -trifluoromethyl)acroleins leads to secondary (trifluoromethyl)allylaminophosphonic acids in moderate to good yields. The method appears to be useful for the preparation of benzylaminophosphonic acids.

Flash vacuum thermolysis of 5-substituted-4,4-diphenyl-3-oxa-1-azabicyclo[3.1.O]hexan-2- ones. A new route to quinolines.

Abstract Thermolysis of bicyclic carbamates produces quinoline derivatives good yields. A two step reaction is described.

Strained molecules: crystal structure of 2,2,3-triphenyl-1-azabicyclo[1.1.0]butane

The first X-ray crystal structure determination of a 1-azabicyclo[1.1.0]butane derivative is reported.

SPECIFIC REDUCTION OF AZIRIDINO KETONES AND IMINES BY ZINC BOROHYDRIDE. ZINC CHELATION BY AZIRIDINES

In protischen Losungsmitteln werden Aziridino-ketimine und -ketone von Zn(BH4)2 100proz. stereospezifisch zu den entsprechenden erythro- Aminen bzw. -Alkoholen reduziert: Bildung des Amins (IV) aus (II), des Alkohols (V) aus (III) und der Alkohole (VI) aus den entsprechenden Ketonen (keine Ausb.-Angaben).