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42908-73-6

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Bare-minimum fluorous mixture synthesis of a stereoisomer library of 4,8,12-trimethylnonadecanols and predictions of NMR spectra of saturated oligoisoprenoid stereoisomers
All four diastereomers of a typical saturated oligoisoprenoid, 4,8,12-trimethylnonadecanol, are made by an iterative three-step cycle with the aid of traceless thionocarbonate fluorous tags to encode configurations. The tags have a minimum number of total fluorine atoms, starting at zero and increasing in increments of one. With suitable acquisition and data processing, each diastereomer exhibits characteristic chemical shifts of methyl resonances in its 1H and 13C NMR spectra. Together, these shifts provide a basis to predict the appearance of the methyl region of the spectrum of every stereoisomer of higher saturated oligoisoprenoids.
Yeh, Edmund A.-H.,Kumli, Eveline,Damodaran, Krishnan,Curran, Dennis P.
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p. 1577 - 1584
(2013/03/28)

The Invention of Radical Reactions. Part XXI. Simple Methods for the Radical Deoxygenation of Primary Alcohols.
Novel radical-chain deoxygenations of primary alcohols are described.The alcohols are acylated with the reagents pentafluorophenyl chlorothionoformate, 2,4,6-trichlorophenyl chlorothionoformate and 4-fluorophenyl chlorothionoformate and the intermediate thionocarbonates are deoxygenated with tributyltin hydride, triphenylsilane, diphenylsilane or phenylsilane in high-yielding reactions.Key Words: Thionocarbonates, Tributyltin hydride, Triphenylsilane, Diphenylsilane, Phenylsilane, Radical deoxygenations.
Barton, Derek H. R.,Blundell, Paul,Dorchak, Joseph,Jang, Doo Ok,Jaszberenyi, Joseph Cs.
p. 8969 - 8984
(2007/10/02)

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Chemical Properties

Boiling Point: 94-95 °C10 mm Hg(lit.)
Flash Point:184 °F
Density: 1.363 g/mL at 25 °C(lit.)
Vapor Pressure: 0.14mmHg at 25°C
Refractive Index: n20/D 1.558(lit.)
PSA: 41.32000
LogP: 2.72820

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