TY - JOUR
T1 - Intermolecular [4 + 2]‐Cycloadditions of Nitroalkenes with Cyclic Olefins. Transformations of Cyclic Nitronates
AU - Denmark, Scott E.
AU - Cramer, Christopher J.
AU - Sternberg, Jeffrey A.
PY - 1986/12/10
Y1 - 1986/12/10
N2 - Nitrocyclohexene undergoes facile SnCl4‐induced, [4 + 2]‐cycloadditions with simple cycloalkenes to produce nitronates. The nitronates can be transformed sterospecifically into a number of other functional groups (alcohol, ketone, oxime, amine) by hydrolytic, reductive, and oxidative processes. The mechanism of the [4 + 2]‐cycloaddition is believed to involve formation of a zwitterionic intermediate which can collapse via competing pathways to form the observed products. 1,3‐Dipolar cycloadditions of the nitronates are described.
AB - Nitrocyclohexene undergoes facile SnCl4‐induced, [4 + 2]‐cycloadditions with simple cycloalkenes to produce nitronates. The nitronates can be transformed sterospecifically into a number of other functional groups (alcohol, ketone, oxime, amine) by hydrolytic, reductive, and oxidative processes. The mechanism of the [4 + 2]‐cycloaddition is believed to involve formation of a zwitterionic intermediate which can collapse via competing pathways to form the observed products. 1,3‐Dipolar cycloadditions of the nitronates are described.
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U2 - 10.1002/hlca.19860690823
DO - 10.1002/hlca.19860690823
M3 - Article
AN - SCOPUS:0001476766
SN - 0018-019X
VL - 69
SP - 1971
EP - 1989
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
IS - 8
ER -