2-Methyl-5,6-dihydro-2H-pyran in the Simmons-Smith reaction
Carbene generated via the Simmons-Smith reaction readily adds to the double bond of 4-methyl-5,6-dihydro-2H-pyran to give the corresponding cycloadduct. We have observed that 2-methyl-5,6-dihydro-2H-pyran, which is isomeric to the former with respect to the position of the methyl group, reacts with methylene iodide and a Zn-Cu couple in a completely different way to give a mixture of four compounds. They are 2-ethyl-5,6-dyhydro-2H-pyran, cis- and trans-2-methyl-3-oxabicyclo-(4.1.0)heptanes, and 2-methyl-2,5,6,7- or 3-methyl-2,3,6,7-tetrahydrooxepine in a ratio of 2:2:5:1. The reaction products were identified by chromatographic mass spectroscopy. Stability considerations under electron impact fragmentation and ionization are compared for the four compounds.
- Research Organization:
- Bashkir State Univ, Ufa (USSR)
- OSTI ID:
- 7004948
- Journal Information:
- Chem. Heterocycl. Compd. (Engl. Transl.); (United States), Vol. 23:4; Other Information: Translated from Khim. Geterotsikl. Soedin.; 23: No. 4, 449-450(Apr 1987)
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
COPPER COMPOUNDS
CATALYTIC EFFECTS
IODINATED ALIPHATIC HYDROCARBONS
PYRANS
HETEROGENEOUS CATALYSIS
ISOMERIZATION
MASS SPECTRA
ZINC COMPOUNDS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
ELECTRON-MOLECULE COLLISIONS
ETHERS
IONIZATION
MOLECULAR IONS
TETRAHYDROFURAN
CATALYSIS
CHARGED PARTICLES
COLLISIONS
ELECTRON COLLISIONS
FURANS
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
IONS
KINETICS
MOLECULE COLLISIONS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
REACTION KINETICS
SPECTRA
TRANSITION ELEMENT COMPOUNDS
YIELDS
400201* - Chemical & Physicochemical Properties
640304 - Atomic
Molecular & Chemical Physics- Collision Phenomena