100073-20-9Relevant academic research and scientific papers
Stereochemistry of the thermal decomposition of (2-(acyloxy)alkyl)triorganostannanes
Jousseaume, Bernard,Noiret, Nicolas,Pereyre, Michel,Francès, Jean-Marc,Pétraud, Michel
, p. 3910 - 3914 (1992)
The stereochemical study of the thermal decomposition of (2-(acyloxy)alkyl)triorganostannanes revealed an anti β-elimination of (acyloxy)triorganostannanes. The process is highly stereospecific and not perturbed by the presence of a possible internal chelation favoring syn elimination. It corresponds to an open transition state. Kinetics of β-elimination in cyclohexyl and norbornyl systems showed that the reaction is much more rapid with a 180° dihedral angle between the metal and the ester group than with a 60° angle between the two. Stabilization of the partial positive charge developed during the transition state occurs mainly through hyperconjugation effect.
A NEW ROUTE TO VINYLTRIBUTYLTIN COMPOUNDS BY FLASH PYROLYSIS OF ALKYLTRIBUTYLTIN ACETATES
Duboudin, J. Georges,Petraud, Michel,Ratier, Max,Trouve, Bruno
, p. C6 - C8 (1985)
Flash pyrolysis of alkyltributyltin acetates, at high temperatures (600-850 deg C) under a moderate vacuum provides a convenient route to vinyltin derivatives.
Multistereocenter-Containing Cyclopentanoids from Ynamides via Oxazolidinone-Controlled Nazarov Cyclization
Manchala, Narasimhulu,Law, Hanson Y. L.,Kerr, Daniel J.,Volpe, Rohan,Lepage, Romain J.,White, Jonathan M.,Krenske, Elizabeth H.,Flynn, Bernard L.
, p. 6511 - 6527 (2017/07/13)
Achieving ready-enantioselective access to multistereocenter-containing cyclopentyl rings is an area of great significance to organic synthesis. In this work, we describe a general protocol for accessing multistereocenter-containing cyclopentanoids from simple N-alkynyloxazolidinones (Ox-ynamides). This protocol involves conversion of Ox-ynamides into Ox-activated divinyl and aryl vinyl ketones that undergo facile Nazarov cyclization with excellent chemo-, regio-, and stereocontrol. The Ox auxiliary directs all aspects of reactivity and selectivity, both in the electrocyclization and in the subsequent transformations of the resulting oxyallyl intermediate. Stereoinduction in the electrocyclization results from a "coupled-torque" mechanism in which rotation of the Ox group, driven by increasing orbital overlap of the nitrogen lone pair with the incipient oxyallyl cation, is coupled with the rotation of the termini of the pentadienyl cation, favoring a particular direction of conrotatory ring closure (torquoselectivity). The associated lone-pair stabilization of the transition state by Ox promotes cyclization of traditionally resistant substrates, broadening the scope of this asymmetric Nazarov cyclization. The Ox group also facilitates the stereo- and regioselective incorporation of nucleophiles (Nu) and dienes, giving more complex, multistereocenter containing cyclopentanoids. Finally, the Ox group is readily removed and recovered or can be converted into other amine functionalities.
SYNTHESIS AND FLASH-PYROLYSIS OF ORGANOTIN -SUBSTITUTED CARBAMATES AND OXALATES
Ratier, Max,Khatmi, Djamel,Duboudin, Jean-Georges
, p. 467 - 482 (2007/10/02)
Organotin -substituted alcohols react readily with aryl(alkyl) isocyanates and oxalyl chloride to give the corrresponding organotin -substituted carbamates and oxalates.Under flash pyrolytic conditions, these esters decompose into vinyltin derivatives.
THERMAL DECOMPOSITION OF ORGANOTIN SULFAMATES: A ONE POT SYNTHESIS OF VINYLTRIBUTYLTIN COMPOUNDS
Ratier, Max,Khatmi, Djamel,Duboudin, J.Georges,Minh, Dao The
, p. 285 - 292 (2007/10/02)
The preparation of some alkyltributyltin sulfamates is described.Thermal decomposition of these compounds provides a route to vinyltributyltin derivatives.
HYDROSTANNATION OF METHYL(CARBOXYSULFAMOYL) TRIETHYLAMMONIUM HYDROXIDE INNER SALT : A NEW ROUTE TO TRIBUTYLTIN ISOCYANATE
Ratier, Max,Khatmi, Djamel,Duboudin, J. Georges,Minh, Dao The
, p. 1929 - 1938 (2007/10/02)
A synthetically useful and facile method for the synthesis of tributyltin isocyanate is described.
Synthese et thermolyse eclair d'esters α-tributylstanniques
Duboudin, J. Georges,Ratier, Max,Trouve, Bruno
, p. 181 - 192 (2007/10/02)
The preparation of some alkyltributyltin acetates and thiocarbonates is described.Flash thermolysis of these compounds at high temperature (600-950 deg C) and under a moderate vacuum, provides a new route to vinyltributyltin derivatives.
