The reaction of 3-substituted oxetanes with nitric acid in dichloromethane

Autor:	Roy B. Moodie, Kevin A. Hylands
Rok vydání:	1997
Předmět:	chemistry.chemical_compound chemistry Nitric acid Nitration Intramolecular force Anhydrous Nitro Organic chemistry Oxetane Medicinal chemistry Catalysis Dichloromethane
Zdroj:	Journal of the Chemical Society, Perkin Transactions 2. :709-714
ISSN:	1364-5471 0300-9580
DOI:	10.1039/a607257g
Popis:	The reactions of 3-phenyloxetane 1, 3-(4-nitrophenyl)oxetane 5 and 3,3-pentamethyleneoxetane 7 with nitric acid in dichloromethane or trichloromethane under anhydrous conditions have been investigated. Quantitative conversion to 2-substituted propane-1,3-diol dinitrates occurs. Compound 1 reacts initially by a mixture of ortho- and para-aromatic nitration and oxetane ring-opening. Aromatic nitrations of 1 and 1,4-dichlorobenzene, the former reacting through its majority hydrogen-bonded complexed form, are approximately sixth order in nitric acid and proceed at a comparable rate. The oxetane ring-opening reactions are approximately second order in nitric acid except in the case of 3-(2-nitrophenyl)oxetane 3, where there is evidence of intramolecular catalysis by the nitro group.
Databáze:	OpenAIRE
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