A Novel Route to 4-Aryl-5,6-dihydro-1,2-oxathiin-2,2-dioxides and Related Heterocyclic Systems

Bonfand, Eric; Motherwell, William B.; Pennell, Andrew M. K.; Uddin, Muhammed K.; Ujjainwalla, Feroze

doi:10.3987/com-97-s63

Cited by 31 publications

(2 citation statements)

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“…Under standard radical conditions, various sulfonates 387 were transformed to oxathiin-2,2-dioxides 388 in moderate yields. 110 Mechanistically, the cascade process was initiated via the addition of the stannyl radical to the terminal alkyne group of 387 to generate the alkenyl radical intermediate 389 , which then underwent a 1,5-aryl transfer to form the S -centered radical 390 . The final 6- endo cyclization of 390 followed by β-fragmentation provided the desired product 388 (Scheme 71).…”

Section: Radical 15-aryl Migrationsmentioning

confidence: 99%

Radical aryl migration reactions and synthetic applications

2015

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Radical aryl migration reactions are of particular interest to the chemical community due to their potential application in radical chemistry and organic synthesis. The neophyl rearrangements used as radical clocks for examining the radical-molecular reactions have been known for decades. The combinations of these migrations with other radical reactions have provided a wide range of novel synthetic methodologies that are complementary to nucleophilic rearrangements. This review will give an overview of various types of radical aryl migrations, with an emphasis on their mechanistic studies from a historical point of view, as well as their application in tandem radical reactions.

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Section: Radical 15-aryl Migrationsmentioning

confidence: 99%

Radical aryl migration reactions and synthetic applications

2015

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“…7 8 9 10 11 This key advancement led to Smiles chemistry being utilized for C–C bond formation in decades to come, with pivotal contributions from Speckamp and Motherwell demonstrating that the reaction can also operate via a radical pathway. 12 13 14 15 16 17…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Smiles Rearrangement: New Opportunities for Arylation

Whalley¹,

Greaney²

2021

Synthesis

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The Smiles rearrangement has undergone a renaissance in recent years providing new avenues for non-canonical arylation techniques in both the radical and polar regimes. This Short Review will discuss recent applications of the reaction (from 2017 onwards), including its relevance to areas such as heterocycle synthesis, functionalisation of alkenes and alkynes as well as glimpses at new directions for the field.

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Synthetic Uses ofR₃MH(M = Ge,Sn,Pb)

Carland

Schiesser

2009

Patai's Chemistry of Functional Groups

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Introduction The Preparation of Novel Trialkylgermanes and Stannanes Trialkyltin Hydrides as Reagents in Radical Chain Reactions Trialkyltin Hydrides in Non‐Radical Chemistry Trialkylgermanium and Lead Hydrides in Synthesis Acknowledgement

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A Novel Route to 4-Aryl-5,6-dihydro-1,2-oxathiin-2,2-dioxides and Related Heterocyclic Systems

Cited by 31 publications

References 0 publications

Radical aryl migration reactions and synthetic applications

Radical aryl migration reactions and synthetic applications

Recent Advances in the Smiles Rearrangement: New Opportunities for Arylation

Synthetic Uses ofR₃MH(M = Ge,Sn,Pb)

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A Novel Route to 4-Aryl-5,6-dihydro-1,2-oxathiin-2,2-dioxides and Related Heterocyclic Systems

Cited by 31 publications

References 0 publications

Radical aryl migration reactions and synthetic applications

Radical aryl migration reactions and synthetic applications

Recent Advances in the Smiles Rearrangement: New Opportunities for Arylation

Synthetic Uses ofR3MH(M = Ge,Sn,Pb)

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Synthetic Uses ofR₃MH(M = Ge,Sn,Pb)