127565-56-4Relevant articles and documents
2-Substituted 3,3-Diethyloxetanes
Fitton, Alan O.,Hill, John,Jane, David E.,Millar, Ross
, p. 2740 - 2750 (2007/10/02)
2-Ethyl-2-(tosyloxymethyl)propanal reacted with vinyl magnesium bromide and with methanolic potassium cyanide to give 3,3-diethyl-2-vinyloxetane and methyl 3,3-diethyloxetane-2-carboximidate respectively.The former was oxidised to 3,3-diethyl-2-(2-oxiranyl)oxetane and the latter was hydrolysed to 3,3-diethyloxetane-2-carboxylic acid (6a).Acid (6a) or the corresponding acid chloride were converted into methyl (6d) and ethyl (6f) esters, and into 3,3-diethyloxetane-2-carboxamide (6e).The methyl ester (6d) reacted with vinyl magnesium bromide to give 3-(3,3-diethyl-2-oxetanyl)penta-1,4-dien-3-ol.The ethyl ester (6f) and amide (6e) were reduced to 3,3-diethyloxetan-2-ylmethanol (7a) and 2-aminomethyl-3,3-diethyloxetane (7b) respectively.On reaction with sodium azide, the tosyl ester of alcohol (7a) yielded the unstable 2-azidomethyl-3,3-diethyloxetane.