1‐<i>tert</i>‐Butylvinyl Trifluoromethanesulfonate: Solvolysis and Rearrangement <i>via</i> a Vinyl Cation

Martı́nez, Antonio Garcı́a; Hanack, Michael; Summerville, Richard H.; Schleyer, Paul von Ragué; Stang, Peter J.

doi:10.1002/anie.197003021

Cited by 21 publications

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References 5 publications

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“…To this date, this is the way all vinyl(enol) triflates are prepared and currently widely used in cross-coupling reactions 20. For us, this opened up the entire spectrum of solvolytic generation of a variety of vinyl cations4a,21 and allowed us to examine cyclic vinyl cations;22 rearrangements of vinyl cations;19b,23 deuterium isotope effects in the generation of vinyl cations24 and the effect different substituents, various solvents and nucleophiles25 have on their generation. We also examined Friedel-Crafts type alkylation of aromatic substrates using enol triflates 26…”

Section: Independent Careermentioning

confidence: 99%

From Solvolysis to Self-Assembly

Stang

2008

J. Org. Chem.

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My sojourn from classical physical-organic chemistry and solvolysis to self-assembly and supramolecular chemistry, over the last forty years, is described. My contributions to unsaturated reactive intermediates, namely vinyl cations and unsaturated carbenes, along with my decade long involvement with polyvalent iodine chemistry, especially alkynyliodonium salts, as well as my more recent research with metal-ligand, coordination driven and directed self-assembly of finite supramolecular ensembles are discussed.

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Section: Independent Careermentioning

confidence: 99%

From Solvolysis to Self-Assembly

Stang

2008

J. Org. Chem.

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Preparation of Vinyl Trifluoromethanesulfonates: 3‐Methyl‐2‐buten‐2‐yl Triflate

Stang

Dueber

2003

Organic Syntheses

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Preparation of Vinyl Trifluoromethanesulfonates: 3‐Methyl‐2‐buten‐2‐yl Triflate intermediate: trifluoromethanesulfonic anhydride reactant: 2.78 g. (0.0352 mole) of anhydrous pyridine solvent: 10 ml. of anhydrous n ‐pentane product: 3‐methyl‐2‐buten‐2‐yl triflate byproduct: 3‐methyl‐1‐buten‐2‐yl triflate product: CH 2 C(CH 3 )OSO 2 CF 3 product: cis and trans C 2 H 5 CHC(C 2 H 5 )OSO 2 CF 3 product: CH 2 C(OSO 2 CF 3 )C(CH 3 ) 3 product: CH 2 C(C 6 H 5 )OSO 2 CF 3 product: CH 2 C(OSO 2 CF 3 )CH 2 (CH 2 ) 2 CH 3 product: CH 2 C(OSO 2 CF 3 )CH(CH 3 ) 2 product: C 6 H 5 C(CH 3 )C(CH 3 )OSO 2 CF 3 ( cis , 18%; trans , 51%) + C 6 H 5 CH(CH 3 )C(OSO 2 CF 3 )CH 2 (31%) product: C 6 H 5 C(CH 3 )C(CH 3 )OSO 2 CF 3 ( trans , 80%; cis , 20%) product: (CH 3 ) 2 CC(CH 3 )OSO 2 CF 3 ( 1 , 70%) + (CH 3 ) 2 CHC(OSO 2 CF 3 )CH 2 ( 2 , 30%) product: 1 (90%) + 2 (10%)

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Vinyl and Allenyl Cations

Stang

1973

Progress in Physical Organic Chemistry

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1‐tert‐Butylvinyl Trifluoromethanesulfonate: Solvolysis and Rearrangement via a Vinyl Cation

Cited by 21 publications

References 5 publications

From Solvolysis to Self-Assembly

From Solvolysis to Self-Assembly

Preparation of Vinyl Trifluoromethanesulfonates: 3‐Methyl‐2‐buten‐2‐yl Triflate

Vinyl and Allenyl Cations

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