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), Journal Name: Chem. Heterocycl. Compd. (Engl. Transl.); (United States) Vol. 23:4; ISSN CHCCA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
640304 -- Atomic
Molecular & Chemical Physics-- Collision Phenomena
74 ATOMIC AND MOLECULAR PHYSICS
CATALYSIS
CATALYTIC EFFECTS
CHARGED PARTICLES
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
COLLISIONS
COPPER COMPOUNDS
ELECTRON COLLISIONS
ELECTRON-MOLECULE COLLISIONS
ETHERS
FURANS
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
HETEROGENEOUS CATALYSIS
IODINATED ALIPHATIC HYDROCARBONS
IONIZATION
IONS
ISOMERIZATION
KINETICS
MASS SPECTRA
MOLECULAR IONS
MOLECULE COLLISIONS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PYRANS
REACTION KINETICS
SPECTRA
TETRAHYDROFURAN
TRANSITION ELEMENT COMPOUNDS
YIELDS
ZINC COMPOUNDS