Stereochemistry of the Diels-Alder reaction of butadiene with cyclopropene
Journal Article
·
· Journal of Organic Chemistry; (USA)
- Syracuse Univ, NY (USA)
1(E)-Deuteriobutadiene and cyclopropene react at 0{degree}C to give 2-endo-deuteriobicyclo(4.1.0)hept-3-ene; 1-(Z)-deuteriobutadiene leads to the 2-exo-deuterio bicyclic product. Analysis of these products through {sup 2}H NMR spectroscopy reveals complete stereospecificity, indicating that the transition structure having an endo orientation of diene and cyclopropene is strongly favored over the alternative exo geometry.
- OSTI ID:
- 7071639
- Journal Information:
- Journal of Organic Chemistry; (USA), Journal Name: Journal of Organic Chemistry; (USA) Vol. 54:22; ISSN JOCEA; ISSN 0022-3263
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALKENES
BUTADIENE
CHEMICAL REACTIONS
CYCLOALKENES
DATA
DATA ANALYSIS
DIELS-ALDER REACTION
DIENES
ETHYLENE
EXPERIMENTAL DATA
HYDROCARBONS
INFORMATION
MAGNETIC RESONANCE
MEASURING INSTRUMENTS
MEASURING METHODS
MEDIUM TEMPERATURE
NUCLEAR MAGNETIC RESONANCE
NUMERICAL DATA
ORGANIC COMPOUNDS
POLYENES
RESONANCE
400201* -- Chemical & Physicochemical Properties
ALKENES
BUTADIENE
CHEMICAL REACTIONS
CYCLOALKENES
DATA
DATA ANALYSIS
DIELS-ALDER REACTION
DIENES
ETHYLENE
EXPERIMENTAL DATA
HYDROCARBONS
INFORMATION
MAGNETIC RESONANCE
MEASURING INSTRUMENTS
MEASURING METHODS
MEDIUM TEMPERATURE
NUCLEAR MAGNETIC RESONANCE
NUMERICAL DATA
ORGANIC COMPOUNDS
POLYENES
RESONANCE