1067-09-0Relevant articles and documents
Organocatalytic Chlorination of Alcohols by P(III)/P(V) Redox Cycling
Longwitz, Lars,Jopp, Stefan,Werner, Thomas
, p. 7863 - 7870 (2019/06/27)
A catalytic system for the chlorination of alcohols under Appel conditions was developed. Benzotrichloride is used as a cheap and readily available chlorinating agent in combination with trioctylphosphane as the catalyst and phenylsilane as the terminal reductant. The reaction has several advantages over other variants of the Appel reaction, e.g., no additional solvent is required and the phosphane reagent is used only in catalytic amounts. In total, 27 different primary, secondary, and tertiary alkyl chlorides were synthesized in yields up to 95%. Under optimized conditions, it was also possible to convert epoxides and an oxetane to the dichlorinated products.
Method for Chlorinating Alcohols
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Page/Page column 5, (2008/12/07)
A process for preparing organic chlorides in which the chlorine atom is bonded to a CH2 group by reacting the corresponding alcohols with thionyl chloride in the presence of a triaylphosphine oxide at a temperature of from 20 to 200° C. and a pressure of from 0.01 to 10 MPa abs, which comprises using the triarylphosphine oxide in a molar ratio to the amount of OH groups to be chlorinated of from 0.0001 to 0.5.
Reactivity of Neopentyl-Like Compounds in the Synthesis of Branched Polyethers
Dale, Johannes,Fredriksen, Siw B.
, p. 278 - 282 (2007/10/02)
Two singly branched symmetrical hexaethers have been synthesized, starting from 2-bromomethyl-2-methyl-1,3-dibromopropane, in a surprisingly efficient one-pot nucleophilic substitution reaction.It is proposed that the expected adverse neopentyl effect is compensated by favourable neighbouring-group participation involving a 'bromonium'-like four-membered-ring transition state.The corresponding trichloride also reacted cleanly, although much more slowly, while the tritosylate gave an oxetane derivative.
UNUSUAL TRIPOD-LIKE LIGANDS. SYNTHESIS OF 2,2-BIS(DIPHENYLPHOSPHINOMETHYL)-1-METHOXYPROPANE AND 2,2-BIS(PHENYLTHIOMETHYL)-1-METHOXYPROPANE
Liu, Shiuh-Tzung,Yieh, Chien-Hung,Lu, Hui-Jane
, p. 261 - 266 (2007/10/02)
By employment of 1,1,1-tris(hydroxymethyl)ethane as the starting material, syntheses of two novel tripod-like terdentates with mixed donor properties, 2,2-Bis(diphenylphosphinomethyl)-1-methoxypropane (P2O) and 2,2-Bis(diphenylphosphinomethyl)-1-methoxypropane (S2O) are reported.Structural confirmation is based on spectroscopic and analytical results.Key words: tripodal ligands; terdentates; organophosphine ligand; organosulfur ligand.
PRODUCTION OF CYCLIC SULFITES AND THEIR TRANSFORMATION INTO SUBSTITUTED TRI(CHLOROMETHYL)METHANES
Bolotov, A. A.,Rodin, A. A.,V'yunov, K. A.,Ginak, A. I.,Sarkisov, Yu. S.
, p. 1812 - 1819 (2007/10/02)
The production of cyclic sulfites from trihydric alcohols and their conversion into chlorides by the action of DMFA-SOCl2 complex are described.By PMR and IR spectroscopy it was shown that cyclic sulfites exist preferentially in the chair conformation with the axial orientation of the S=O bond.It was established that the chlorides are formed in two parallel paths, i.e. directly from trihydric alcohols and their cyclic sulfites.