85335-71-3Relevant academic research and scientific papers
Evaluation of cyclopentyl methyl ether (CPME) as a solvent for radical reactions
Kobayashi, Shoji,Kuroda, Hiroyuki,Ohtsuka, Yuta,Kashihara, Takashi,Masuyama, Araki,Watanabe, Kiyoshi
, p. 2251 - 2259 (2013/03/29)
We have explored the potential of cyclopentyl methyl ether (CPME) as a solvent for radical reactions. Hydrostannation, hydrosilylation, hydrothiolation, and tributyltin hydride mediated reductions were successfully carried out in CPME. GC-MS analysis indicated that CPME degraded into methyl pentanoate, cyclopentanone, 2-cyclopenten-1-ol, and cyclopentanol under thermal radical conditions, albeit only slightly. We also achieved radical-containing one-pot reactions in CPME as a demonstration of its applicability to multi-step reactions.
The invention of radical reactions. Part XXIV. Relative rates of acylation and radical deoxygenation of secondary alcohols
Barton,Dorchak,Jaszberenyi
, p. 7435 - 7446 (2007/10/02)
Secondary alcohols were transformed into various thiocarbonyl derivatives. Reduction of these compounds using tributyltin hydride and an initiator afforded the corresponding deoxy-compounds. Half-life and competitive measurements showed that all these reactions were fast and could be run to completion.
Radical cation reactions associated with the thiocarbonyl group
Barton,Dalko,Gero
, p. 1883 - 1886 (2007/10/02)
The radical cation reactions of different thiocarbonyl compounds were examined. Compounds 7, 8, 11, 14 and 18 underwent a radical cation fragmentation in a photoinduced electron transfer (PET) reaction, in the presence of tris(4-bromophenyl)aminium hexachloroantimonate.
NUCLEIC ACID RELATED COMPOUNDS. 42. A GENERAL PROCEDURE FOR THE EFFICIENT DEOXYGENATION OF SECONDARY ALCOHOLS. REGIOSPECIFIC AND STEREOSELECTIVE CONVERSION OF RIBONUCLEOSIDES TO 2 prime -DEOXYNUCLEOSIDES.
Robins,Wilson,Hansske
, p. 4059 - 4065 (2007/10/02)
Treatment of unhindered secondary alcohols with phenoxythiocarbonyl chloride (phenyl chlorothionocarbonate) in pyridine/dichloromethane, or in acetonitrile with 4-dimethylaminopyridine catalysis for hindered alcohols, gave clean conversion to their O-phenoxythiocarbonyl derivatives. Reductive deoxygenation of these phenyl thionocarbonate esters proceeded smoothly, using tri-n-butyltin hydride and a free radical initiator in warm toluene. Overall conversion yields ranged from 57 to 78% for the naturally occurring nucleosides, nucleoside antibiotics, and methyl beta -D-ribofuranoside.
