The mechanism of formation of Grignard reagents: trapping of free alkyl radical intermediates by reaction with tetramethylpiperidine-N-oxyl

1989 ◽  
Vol 111 (14) ◽  
pp. 5405-5412 ◽  
Author(s):  
Karen S. Root ◽  
Craig L. Hill ◽  
Lynette M. Lawrence ◽  
George M. Whitesides
Keyword(s):  
Alkyl Radical ◽  
Grignard Reagents ◽  
Mechanism Of Formation ◽  
Radical Intermediates

Design and Development of Fe-Catalyzed Intra- and Intermolecular Carbofunctionalization of Vinyl Cyclopropanes

2019 ◽  
Author(s):  
Lei Liu ◽  
Wes Lee ◽  
Mingbin Yuan ◽  
Chris Acha ◽  
Michael B. Geherty ◽  
...  
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Mechanistic Studies ◽  
Radical Intermediates ◽  
Design And Implementation ◽  
Solvent Cage ◽  
Radical Cascade ◽  
Radical Processes

Design and implementation of the first (asymmetric) Fe-catalyzed intra- and intermolecular difunctionalization of vinyl cyclopropanes (VCPs) with alkyl halides and aryl Grignard reagents has been realized via a mechanistically driven approach. Mechanistic studies support the diffusion of the alkyl radical intermediates out of the solvent cage to participate in an intra- or -intermolecular radical cascade with the VCP followed by re-entering the Fe radical cross-coupling cycle to undergo selective C(sp2)-C(sp3) bond formation. Overall, we provide new design principles for Fe-mediated radical processes and underscore the potential of using combined computations and experiments to accelerate the development of challenging transformations.

Mechanism of formation of Grignard reagents. Kinetics of reaction of alkyl halides in diethyl ether with magnesium

1980 ◽  
Vol 102 (1) ◽  
pp. 217-226 ◽  
Author(s):  
Harold R. Rogers ◽  
Craig L. Hill ◽  
Yuzo Fujiwara ◽  
Randall J. Rogers ◽  
H. Lee Mitchell ◽  
...  
Keyword(s):  
Diethyl Ether ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Mechanism Of Formation ◽  
Kinetics Of Reaction ◽  
Kinetics Of

Mechanism of formation of Grignard reagents. Corrosion of metallic magnesium by alkyl halides in ethers

1980 ◽  
Vol 45 (6) ◽  
pp. 1020-1028 ◽  
Author(s):  
Craig L. Hill ◽  
John B. Vander Sande ◽  
George M. Whitesides
Keyword(s):  
Alkyl Halides ◽  
Grignard Reagents ◽  
Mechanism Of Formation ◽  
Metallic Magnesium

Mechanism of formation of Grignard reagents

1978 ◽  
Vol 100 (10) ◽  
pp. 3163-3166 ◽  
Author(s):  
E. A. Vogler ◽  
R. L. Stein ◽  
J. M. Hayes
Keyword(s):  
Grignard Reagents ◽  
Mechanism Of Formation
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