Tetrahedron p. 4355 - 4360 (1991)
Update date:2022-08-04
Topics:
Bessiere, Yvonne
Bessard, Yves
Kotani, Takayuki
Schlosser, Manfred
Three new model substrates of the chlorofluorocyclopropane type (6, 11 and 14) were submitted to silver ion-assisted ring opening.No rearrangement, but only fragmentation or direct solvolysis was found to take place.In the latter case, primary rather than tertiary 2-fluoroallyl alcohols are formed almost exclusively.Nucleophilic attack at the unsubstituted terminus of the 2-fluoroallyl cation is apparently favored for steric reasons.
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Doi:10.1021/ja0661010
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