Abstract
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.
Original language | English (US) |
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Pages (from-to) | 1971-1989 |
Number of pages | 19 |
Journal | Helvetica Chimica Acta |
Volume | 69 |
Issue number | 8 |
DOIs | |
State | Published - Dec 10 1986 |
ASJC Scopus subject areas
- Catalysis
- Biochemistry
- Drug Discovery
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry