95672-69-8Relevant academic research and scientific papers
Proton and Carbon NMR Spectra and Stereochemical Assigments for 3,5-disubstituted Nortricyclenes
Chizhov, A. O.,Zefirov, Nikolai S.,Zyk, N.V.
, p. 5647 - 5655 (2007/10/02)
Proton (1H) and carbon (13C) nuclear magnetic resonanse (NMR) spectra of over 80 substituted nortricyclenes (including newly preparated stereoisomers) have been analyzed, leading to an empirical method for calculating the proton chemical shifts for endo-3 protons of exo-5- and endo-5, exo-3-disubstituted nortricyclenes.This calculation method has been used to established the stereochemistry of other 3,5-disubstituted compounds of previously unknown or ircorrectly assignated structures.Altough the size of the data base for 13C shifts is smaller, it does appear that γ-gauche and related effects are clearly insufficient to explain theseshift changes.
ADDITION OF ACETYL NITRATE TO CYCLIC DIENES
Zyk, N. V.,Nikulin, A. V.,Ugrak, B. I.,Borisenko, A. A.,Zefirov, N. S.
, p. 1082 - 1087 (2007/10/02)
The addition of acetyl nitrate to cyclopentadiene takes place by a 1,4-addition mechanism, giving a mixture of cis and trans stereoisomers.The products from the addition of acetyl nitrate to 1,5-cyclooctadiene and norbornadiene were studied in detail.The obtained data are interpreted from the standpoint of the previously proposed mechanism, involving a stage of -cycloaddition of the nitronium ion at the double bond and subsequent skeletal, hydride, and homoallylic rearrangements in the obtained cyclic adduct.
REACTION OF ACETYL NITRATE WITH QUADRICYCLENE
Zyk, N. V.,Nikulin, A. V.,Kolbasenko, S. I.,Zefirov, N. S.
, p. 1881 - 1884 (2007/10/02)
The reaction of acetyl nitrate with tetracyclo2,7-04,6>heptane (quadricyclene) takes place in two directions with initial electrophilic attack both by the nitronium ion and by the proton, giving the series of corresponding substituted derivatives of nortricyclene.
