The reaction of some 3- and 4-fluorooexetanes with acids

Tarrant, Paul; Bull, Richard

doi:10.1016/s0022-1139(00)83066-3

Cited by 19 publications

(2 citation statements)

References 6 publications

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“…appeared (33) concerning the ring-opening of partially fluorinated oxetanes with AlC13. Likewise, others in our laboratory have found (34) that a Lewis acid alone (SbF5) converts 1-3 to dimers and trimers, presumably through a fluoride-ion abstraction mechanism; this should not contribute in the current Bronsted-Lowry acid work since the amount of molecular SbF5 in an HF mixture is negligible (4).…”

Section: Resultsmentioning

confidence: 99%

Superacid-induced ring-opening reactions of fluorinated heterocycles

Kotun¹,

DesMarteau²

1989

Can. J. Chem.

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This paper is dedicated to Professor Ronald J . Gillespie on the occasion of his 65th birthday STEFAN P. KOTUN and DARRYL D. DESMARTEAU. Can. J. Chem. 67, 1724Chem. 67, (1989. HF/AsFS and HF/SbFS superacid mixtures react with fluorinated small-ring heterocycles such as 1,2-oxazetidines and oxetanes with consequent addition of HF to give alcohol and amine ring-opened products in high yield. Excess HF serves as solvent and reactant. Ring compounds containing both nitrogen and oxygen as heteroatoms protonate predominantly on nitrogen; a case with competing 0-protonation arises in the case of a chloro-substituted oxazetidine. In general, rings containing two heteroatoms retain the heteroatom-heteroatom bond and it is a carbon-heteroatom bond that opens. The resulting OH and NH functional groups are not protonated and lost in the superacid medium due to the instability of the highly fluorinated cations that would be left behind. Most of the heterocycles react at or below room temperature, although the very weakly basic 2,2-bis(trifluoromethyl)-3,3,4,4-tetrafluorooxetane requires the stronger HF/SbFS superacid system and more severe conditions. Key words: superacids, hydrogen fluoride, ring opening, fluorinated oxazetidines, fluorinated oxetanes.

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Section: Resultsmentioning

confidence: 99%

Superacid-induced ring-opening reactions of fluorinated heterocycles

Kotun¹,

DesMarteau²

1989

Can. J. Chem.

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“…The reaction of 2,2-bis(trifluoromethyl)polyfluorooxetanes with AlCl 3 was published several years ago. 161 In most cases ring-opening reactions are accompanied by formation of chlorine-containing products.…”

Section: Heterocyclic Compoundsmentioning

confidence: 99%