Michael condensation of α-nitroalkenes with various nucleophiles, followed by the addition of trimethylchlorosilane, led to novel syntheses of 4,5-dihydroisoxazoles via cycloadditions of silyl nitronates.

The Reactions of Primary Nitroparaffins with Isocyanates1

A novel strategy for the synthesis of 4,5-dihydroisoxazoles via conjugate additions to α-nitroalkenes

Dehydration reactions of hydroxamic acids with unsaturated ethers have been studied. The reaction of hydroxamic acids with ethoxyacetylene or methylketene diethylacetal led to the formation of corresponding isocyanates, along with ethyl acetate or ethyl propionate and ethanol, through the intermediate of addition compounds of hydroxamic acids and the dehydrating reagents. The reaction of hydroxamic acids with n-butyl vinyl ether, on the other hand, led to the formation of dihydroxamic acids, along with acetaldoxime and acetaldehyde dibutyl-acetal. This type of reaction was further extended to the reactions of hydroxamic acids with propenyl ether, acetals and aldehydes, and the formation of dihydroxamic acids was confirmed.

Dehydration Reaction of Hydroxamic Acids with Unsaturated Ethers

The Use of Templates in Combinatorial Chemistry for the Solid‐Phase Synthesis of Multiple Core Structure Libraries

The reactions of [2+3] cycloaddition of nitrile oxides to polyvinylgermanes proceed regioselectively and afford 5-Ge substituted polyisoxazolinylgermanes. The structure of products obtained was confirmed by H NMR and, in the case of 6, by X-ray analysis. INTRODUCTION We have shown previously that vinyland allyl-germanes readily react with nitrile oxides (Mukaiyama-Hoshito method [1]) to give 5-germyl-isoxazolines-2 with good yields [2], Now we are reporting the cycloaddition of nitrile oxides to vinylgermanes containing two and four vinyl groups and to a digermane containing six vinyl groups. It opens a simple way to di-, tetraand hexaisoxazolinylgermanes. RESULTS AND DISCUSSION Divinyldiethylgermane, tetravinylgermane and hexavinyldigermane interact with nitrile oxides to give the germanes containing several isoxazoline rings in good yields:

Synthesis of polyisoxazolinylgermanes

3-nitropropanal, 3-nitropropanol, and 3-nitropropanal dimethyl acetal



product: 3-Nitropropanal




reactant: 334 mL (280 g, 0500 mol) of acrolein




product: 3-nitropropanol




reactant: 637 g (0600 mol) of trimethyl orthoformate




product: 3-nitropropanal dimethyl acetal




product: 3-nitropropanal diethyl acetal





Keywords:

acetal (and thioacetal) formation;
acetal (and thioacetal) formation;
addition, to CCCO and CCCN;
reduction, CO  CHOH

The Reactions of Primary Nitroparaffins with Isocyanates1

Citations

A novel strategy for the synthesis of 4,5-dihydroisoxazoles via conjugate additions to α-nitroalkenes

Dehydration Reaction of Hydroxamic Acids with Unsaturated Ethers

The Use of Templates in Combinatorial Chemistry for the Solid‐Phase Synthesis of Multiple Core Structure Libraries

Synthesis of polyisoxazolinylgermanes

3‐Nitropropanal, 3‐Nitropropanol, and 3‐Nitropropanal Dimethyl Acetal

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