62872-54-2Relevant academic research and scientific papers
Phosphonomethylation of Cyclohexene Oxides
Montchamp, Jean-Luc,Migaud, Marie E.,Frost, John W.
, p. 7679 - 7684 (1993)
The tradeoff between synthetic directness and regioselectivity during oxirane ring opening is examined for two strategies used to phosphonomethylate cyclohexene oxide and substituted cyclohexene oxides derived from quinic acid and myo-inositol.Direct phosphonomethylation of the cyclohexene oxides utilizes diisopropyl lithiomethanephosphonate ((C3H7O)2P(O)CH2Li) in combination with boron trifluoride.Another more indirect route to phosphonomethylation begins with reaction of the cyclohexene oxides with (lithiomethyl)dimesitylborane (Mes2BCH2Li).In both reactions, boron plays a key role as either a Lewis acid during opening of the oxirane (diisopropyl lithiomethanephosphonate/boron trifluoride) or as a stabilizer of an adjacent carbanion in the attacking nucleophile .Regioselectivies for oxirane ring opening using diisopropyl lithiomethanephosphonate/boron trifluoride can be quite modest.By contrast, oxirane ring openings employing (lithiomethyl)dimesitylborane are uniform in the high degree of regioselectivity which is achieved.Factors which might influence the observed regioselectivities during nucleophilic attack on the cyclohexene oxides are also discussed.
Reactions of Norcarane and of Norborn-2-ene with Iodine(I) Azide and Iodine(I) Chloride
Cambie, Richard C.,Dixon, Graham,Rutledge, Peter S.,Woodgate, Paul D.
, p. 961 - 966 (2007/10/02)
With iodine(I) azide or iodine(I) chloride norcarane gives products of ring opening as well as those of fragmentation followed by addition.Reactions of norborn-2-ene with iodine(I) azide under conditions which favour either an ionic or a radical path have
