Several Monoterpenoid Bromination Products
2014
Frolova, L. L. | Bezuglaya, L. V. | Alekseev, I. N. | Slepukhin, P. A. | Kuchin, A. V.
2α-Bromo,10β-pinanone-3 and 3α-bromo,10β-pinanone-4 were formed with 92–98% selectivity by bromination of isopinocamphone and cis-verbanone with Meldrum’s acid dibromide. 3α-Bromo, 10β-pinanone-4 was prepared for the first time. Its structure was confirmed by an XSA. Bromination of menthone by Meldrum’s acid dibromide formed mainly a mixture of diastereomeric 2-bromomenthones in a 2:1 ratio. Oxidative bromination of isopinocampheol by Ce(III)–LiBr–H₂O₂caused rearrangement of the pinane structure into bornane and formed a mixture of 6-endo- and 6-exo-bromocamphor in a 5:1 ratio.
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