Reasons for the regioselectivity in the nucleophilic substitution of 5,5-di(chloromethyl)-1,3-dioxane

Journal Article · Sat Nov 19 23:00:00 EST 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5950426

Bresler, I G; Orlovskii, V V; Khusainov, M A; Kantor, E A; Akhmatdinov, R T; Rakhmankulov, D L

2-R-5-Chloromethyl-5-iodomethyl-1,3-dioxanes are formed with small yields in the reaction of 2-R-5,5-di(chloromethyl)-1,3-dioxanes with sodium iodide in acetone. Substitution takes place mainly (R=C/sub 6/H/sub 5/) or exclusively (R=C/sub 4/H/sub 9/) in the equatorial chloromethyl group. The nycleophilic substitution of 5,5-di(chloromethyl)-1,3-dioxane was investigated by CNDO/2 and MINDO/3 methods. It is suggested on the basis of the form of the potential function that the reason for the regioselectivity is the destabilizing interaction between the highest occupied molecular orbitals of the attaching or leaving anion and the highest molecular orbitals of the substrate.

• Research Organization: Ufa Petroleum Institute (USSR)
• OSTI ID: 5950426
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:6; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALKALI METAL COMPOUNDS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHLORIDES
CHLORINATION
CHLORINE COMPOUNDS
COHERENT SCATTERING
CONFORMATIONAL CHANGES
CRYSTAL LATTICES
CRYSTAL STRUCTURE
DECHLORINATION
DEHALOGENATION
DIFFRACTION
ENERGY
HALIDES
HALOGEN COMPOUNDS
HALOGENATION
HETEROCYCLIC COMPOUNDS
INORGANIC PHOSPHORS
IODIDES
IODINE COMPOUNDS
MATHEMATICAL MODELS
MOLECULAR MODELS
MOLECULAR STRUCTURE
MONOCLINIC LATTICES
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
PHOSPHORS
POTENTIAL ENERGY
SCATTERING
SODIUM CHLORIDES
SODIUM COMPOUNDS
SODIUM IODIDES
STRUCTURAL CHEMICAL ANALYSIS
X-RAY DIFFRACTION