590-50-1Relevant articles and documents
Bartok
, p. 139 (1979)
Palladium-Catalyzed Aerobic Anti-Markovnikov Oxidation of Aliphatic Alkenes to Terminal Acetals
Komori, Saki,Yamaguchi, Yoshiko,Kataoka, Yasutaka,Ura, Yasuyuki
, p. 3093 - 3099 (2019/03/29)
Terminal acetals were selectively synthesized from various unbiased aliphatic terminal alkenes and 1,2-, 1,3-, or 1,4-diols using a PdCl2(MeCN)2/CuCl catalyst system in the presence of p-toluquinone under 1 atm of O2 and mild reaction conditions. The slow addition of terminal alkenes suppressed the isomerization to internal alkenes successfully. Electron-deficient cyclic alkenes, such as p-toluquinone, were key additives to enhance the catalytic activity and the anti-Markovnikov selectivity. The halogen groups in the alkenes were found to operate as directing groups, suppressing isomerization and increasing the selectivity efficiently.
Complete ozonolysis of alkyl substituted ethenes at -60°C: Distributions of ozonide and oligomeric products
Barton, Matthew,Ebdon, John R.,Foster, Andrew B.,Rimmer, Steve
, p. 1323 - 1329 (2007/10/03)
The distribution of ozonidc and oligomeric structures formed on complete ozonolysis of alkenes in a non-participating solvent at -60°C is governed by the alkyl substitution around the carbon-carbon double bond. The ozonolysis of a 1,1-alkyl substituted ethene generally favours the formation of an ozonide (a 1,2,4-trioxolane). Whereas the ozonolysis of a 1,1,2-alkyl substituted ethene also produces ozonide, a considerable amount of the ozonised products are oligomeric in nature. For example, the ozonolysis of 3-methylpent-2-ene in solution to high conversion in pentane yields oligomers with structural units derived from the fragmentation products of the primary ozonide (a 1,2,3-trioxolane) which are namely butanone carbonyl oxide and acetaldehyde; these can be characterised by electrospray ionisation mass spectroscopy (ESI-MS) under soft ionisation conditions. The predominant oligomers formed are rich in carbonyl oxide units (80 + mol%) and are cyclic in nature. A small proportion of the oligomers formed are open chain compounds with end groups that suggest that chain termination is brought about either by water or by hydrogen peroxide. Residual water in the solvent will react with the carbonyl oxides to produce 2-methoxybut-2-yl hydroperoxide, which we propose readily decomposes generating hydrogen peroxide. A significant yield of oligomers also is obtained from the ozonolysis of a 1,2-alkyl substituted ethene. The ozonolysis of trans-hex-2-ene in pentane yields oligomers containing up to four structural units and are predicted to be mainly cyclic. The Royal Society of Chemistry 2005.
