Conformational analysis of sulfur-carbon-phosphorus anomeric interactions. 3. The conformational preference of the diphenylphosphinoyl group in cyclohexane

…, NA Lopez-Nunez, RS Glass, A Petsom…

Index: Juaristi, Eusebio; Lopez-Nunez, Norma A.; Glass, Richard S.; Petsom, Amorn; Hutchins, Robert O.; Stercho, Juriy P. Journal of Organic Chemistry, 1986 , vol. 51, # 8 p. 1357 - 1360

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Citation Number: 21

Abstract

Concerning the mechanism of the fluorinations, NOz+ is capable of bringing about bromide abstraction from the C-Br bonds followed by quenching of the bridgehead carbocations by fluoride from the pyridinium polyhydrogen fluoride reagent. This accounts for the SN1 type fluorine exchange reaction of 1, 4, 9-tribromodiamantane. The nitronium ion is, however, also capable of attacking the tertiary bridgehead CH bond at C,. The transition state must ...