Benzyl- and 2- and 4-nitrobenzylcyclopropanes and their reaction with organic acids
The nitration of benzylcyclopropane and its transformations in organic acids were studied. Under the conditions of electrophilic nitration the small ring is preserved while the ratio of the o- and p-nitrophenyl derivatives amount to 1.1:1. The reaction of benzylcyclopropane with formic and acetic acids takes place with the addition of the fragments of the acid at the 1,2-bond of the three-carbon ring; o- and p-nitrobenzylcyclopropanes do not react with formic and acetic acids, with trifluoroacetic acid they form trifluoroacetates, and in the case of the ortho-substituted isomer nucleophilic assistance from the nitro group is observed. Significant differences in the behavior of phenylcyclopropane and benzylcyclopropane due to the destruction of the conjugation between the fragments in the molecule are observed in the acid-catalyzed reactions.
- Research Organization:
- M.V. Lomonosov Moscow State Univ. (USSR)
- OSTI ID:
- 5887807
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:7; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ACETIC ACID
ACTIVATION ENERGY
ALKANES
CARBOXYLIC ACIDS
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHROMATOGRAPHY
CYCLOALKANES
ENERGY
FORMIC ACID
HYDROCARBONS
INFRARED SPECTRA
ISOMERIZATION
ISOMERS
KINETICS
MONOCARBOXYLIC ACIDS
NITRATION
NITRO COMPOUNDS
NMR SPECTRA
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
REACTION KINETICS
SEPARATION PROCESSES
SPECTRA