One electron C-C bond forming reactions allylstannanes: Scope and limitations

Keck, Gary E.; Enholm, Eric J.; Yates, John B.; Wiley, Michael R.

doi:10.1016/s0040-4020(01)97185-6

Cited by 296 publications

(112 citation statements)

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“…To extend the versatility of these procedures, the use of allyl stannanes was also investigated (29). It was suspected that the allyl stannanes might be more reactive than simple monosubstituted alkenes, a result that was confirmed experimentally when either allyltri-11-butylstannane or methallyltri-n-butylstannane were employed with 4, 7 , and 21 respectively.…”

Section: Resultsmentioning

confidence: 99%

Free-radical based cycloalkanol synthesis and annulation from thioacetal precursors

Yadav¹,

Fallis²

1991

Can. J. Chem.

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A general procedure for the synthesis of diverse cyclopentanols via free-radical cyclization of unsaturated 1,3-oxathiolanes and I ,3-oxathiolan-5-ones is described. The scope of these reactions, including preliminary rate studies that indicate that the 1,3-oxathiolan-5-ones cyclize at a useful rate (I .4 X lo6 M-I S -I at 80°C), has been examined. This permits the rapid assembly, by intramolecular annulation, of various additional ring systems, including bicyclo[3.

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Section: Resultsmentioning

confidence: 99%

Free-radical based cycloalkanol synthesis and annulation from thioacetal precursors

Yadav¹,

Fallis²

1991

Can. J. Chem.

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“…Allyltin compounds are unique players in radical chemistry, since they are able to serve both as radical acceptors and at the same time as radical chain mediators to provide tin radicals [27]. Because of the nucleophilic nature of ordinary alkyl radicals, the addition of an alkyl radical to tributylallyltin is not very fast, yet fast enough to transfer the radical chain [28].…”

Section: Multicomponent Coupling Reactions Mediated By Group 14 Radicalsmentioning

confidence: 99%

Free‐Radical‐Mediated Multicomponent Coupling Reactions

Tojino

Ryu

2005

Multicomponent Reactions

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“…In the eighties, Keck and Migita showed that the allylation of organic halides with allyltri-n-butylstannane pro-vided a powerful and selective synthetic method for introducing allyl groups [18][19][20] . The reactions of allyltri-n-butylstannane with alkyl halides, especially with polyhaloalkanes, a-haloesters or a-halonitriles took place under mild conditions in excellent yields.…”

Section: Displacement Of the Bromine By Allyl End Groupsmentioning

confidence: 99%