Regioselectivity of the bromination of 1-oxo-1,2,3,4-tetrahydronaphthalene and 6,7-dimethyl-1-oxo-1,2,3,4-tetrahydronaphthalene, and thiabiscyclanones synthesis on their basis

doi:10.2298/JSC0406421P

Paper

Regioselectivity of the bromination of 1-oxo-1,2,3,4-tetrahydronaphthalene and 6,7-dimethyl-1-oxo-1,2,3,4-tetrahydronaphthalene, and thiabiscyclanones synthesis on their basis

Published 2004 · A. Pankratov, O. V. Fedotova, A. V. Barabanova

Journal of The Serbian Chemical Society

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Abstract

On the basis of quantum chemical (PM3 and RHF/6-31G*) study, the regioselectivity of the bromination of 1-oxo-1,2,3,4-tetrahydronaphthalene (1) and 6,7-dimethyl-1-oxo-1,2,3,4-tetra- hydronaphthalene (2) at their alicyclic and aromatic fragments was quantum chemically substanti- ated and confirmed experimentally. It was found that the above compounds undergo aromatic at the -methylene position. The conditions for bromination at the positions 5, 8 of benzannelated ring were established. For the first time, non- and 2,2'-dibromosubstituted with respect to the oxo group bis(6,7-dimethyl-1-oxo-1,2,3,4-tetrahydronaphth-2-yl) sulphides (7, 8a, b) were obtained. The latter were found to show promise as stabilizing agents for the storage of cholera sera.

Study Snapshot

The bromination of 1-oxo-1,2,3,4-tetrahydronaphthalene and 6,7-dimethyl-1-oxo-1,2,3,4-tetrahydronaphthalene leads to regioselective synthesis of thiabiscyclanones

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Regioselectivity of the bromination of 1-oxo-1,2,3,4-tetrahydronaphthalene and 6,7-dimethyl-1-oxo-1,2,3,4-tetrahydronaphthalene, and thiabiscyclanones synthesis on their basis

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References

Electrophilic aromatic substitution regioselectivity for benzene derivatives in terms of cationic localization energies from semiempirical quantum chemical computations

The cationic localization energies of monosubstituted benzenes with nitronium cation correlate linearly with nitration isomeric product yields, supporting the Arrhenius equation and linear free energy relationships.

MOPAC: A semiempirical molecular orbital program

MOPAC is a semiempirical molecular orbital program for studying chemical reactions involving molecules, ions, and linear polymers, enabling calculations of vibrational spectra, thermodynamic quantities, isotopic substitution effects, and force constants.

Optimization of parameters for semiempirical methods II. Applications

The new MNDO-PM3 method optimizes MNDO/AM1-type parameters for twelve elements, reducing average errors in predicted heats of formation and experimental values.

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