Published September 2006
| Version v1
Journal article
Oxidation of tertiary homoallylic alcohols by thallium trinitrate: fragmentation versus ring contraction
Creators
- 1. Sao Paulo Univ., SP (Brazil). Inst. de Quimica. Dept. de Quimica Fundamental
- 2. Universidade Estadual de Campinas, SP (Brazil). Inst. de Quimica
Description
The oxidation of tertiary homoallylic alcohols with thallium trinitrate (TTN) was investigated. The alcohols bearing an allylic methyl group lose a molecule of acetone via a fragmentation reaction that leads to isomeric secondary allylic alcohols as major products, together with their corresponding acetylated derivatives. On the other hand, treating analogous tertiary alcohols without the allylic methyl group with TTN gives indans, through a ring contraction reaction. (author)
Additional details
Identifiers
Publishing Information
- Journal Title
- Journal of the Brazilian Chemical Society
- Journal Volume
- 17
- Journal Issue
- 5
- Journal Page Range
- p. 981-988
- ISSN
- 0103-5053
- CODEN
- JOCSET
INIS
- Country of Publication
- Brazil
- Country of Input or Organization
- Brazil
- INIS RN
- 38028208
- Subject category
- S75: CONDENSED MATTER PHYSICS, SUPERCONDUCTIVITY AND SUPERFLUIDITY;
- Descriptors DEI
- ACETONE; BENZOPHENONE; CARBON 13; CYCLIZATION; GAS CHROMATOGRAPHY; HYDROGEN 1; INDAN; INFRARED SPECTRA; ISOMER SHIFT; NMR SPECTRA; THALLIUM
- Descriptors DEC
- AROMATICS; CARBON ISOTOPES; CHEMICAL REACTIONS; CHROMATOGRAPHY; ELEMENTS; EVEN-ODD NUCLEI; HYDROCARBONS; HYDROGEN ISOTOPES; ISOTOPES; KETONES; LIGHT NUCLEI; METALS; NUCLEI; ODD-EVEN NUCLEI; ORGANIC COMPOUNDS; SEPARATION PROCESSES; SPECTRA; STABLE ISOTOPES
Optional Information
- Notes
- 19 refs., 3 tabs., 5 schms. Also available from http://www.scielo.br/pdf/jbchs/v17n5/23.pdf. Access on: 05 Feb 2007