Addition of sulfonyl iodides to allenes

Truce, William E.; Heuring, D. L.; Wolf, Gordon C.

doi:10.1021/jo00916a027

Cited by 61 publications

(27 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…9 In contrast, iodine rapidly reacts with sulfinate to give sulfonyl iodide. 10 To confirm this reaction pathway the following two reactions were carried out. In the first reaction, the bromine color rapidly faded when it was dropped into a dichloromethane solution of diphenyldisulfide, but iodine did not react with diphenyldisulfide under both solvent and solvent-free conditions.…”

Section: Equationmentioning

confidence: 98%

New and Facile Synthesis of Thiosulfonates from Sulfinate/Disulfide/I2 System

Fujiki¹,

Tanifuji²,

Sasaki³

et al. 2002

Synthesis

View full text Add to dashboard Cite

show abstract

Section: Equationmentioning

confidence: 98%

New and Facile Synthesis of Thiosulfonates from Sulfinate/Disulfide/I2 System

Fujiki¹,

Tanifuji²,

Sasaki³

et al. 2002

Synthesis

View full text Add to dashboard Cite

show abstract

“…The reaction mixture was heated to reflux for 5 h. t-BuOH (0.24 mL, 2.5 mmol) was added at 0 8C and the solution was stirred for 15 min at room temperature. After addition of freshly prepared para-toluenesulfonyl iodide [32] (846 mg, 30 mmol) at 0 8C. Air (60 mL, 0.5 mmol O 2 ) was introduced over 90 min through a needle placed just above the reaction surface.…”

Section: General Procedures D (Iodination)mentioning

confidence: 99%

An Efficient Radical Procedure for the Halogenation and Chalcogenation of B‐Alkylcatecholboranes

et al. 2008

View full text Add to dashboard Cite

An efficient formal anti-Markovnikov addition of HX (X = Cl, Br, I, SR and SeR) to olefins under mild reaction conditions is described. The procedure is based on the hydroboration of alkenes with catecholborane. The conversion of the intermediate B-alkylcatecholboranes to the corresponding halides, sulfides and selenides is based on a common process, i.e., generation of a radical from the alkylborane followed by abstraction of a heteroatom from an aromatic sulfonyl reagent. The efficiency of these radical reactions is remarkable. The mildness of the reaction conditions is well illustrated by the preparation of iodoalkanes. Despite the notorious reactivity of iodoalkanes under radical reaction conditions, no product degradation was observed.

show abstract

“…Aryl‐ and alkylsulfonyl halides undergo bond homolysis,14 and the resulting sulfonyl radicals are subsequently added to substituted and unsubstituted olefins 15–24. Percec pointed out that the homolysis of the sulfonyl halide can be initiated thermally 25.…”

Section: Introductionmentioning

confidence: 99%

Radical ring‐opening polymerization of five‐membered cyclic vinyl sulfone using p‐toluenesulfonyl halides

Tanaka

Furusho

Endō

2012

J. Polym. Sci. A Polym. Chem.

View full text Add to dashboard Cite

Radical ring-opening polymerizations of a five-membered cyclic vinyl sulfone monomer, 2-vinylthiolane-1,1-dioxide (VTDO), was carried out by using p-toluenesulfonyl iodide (TosI) and bromide (TosBr) as radical initiators, and the corresponding ring-opened polymer (PVTDO) was obtained. Both TosI and TosBr were found to work as the radical initiators for the polymerization of VTDO in bulk. The use of TosI gave PVTDOs with a broad, multimodal distribution of molecular weight in low yields. When 10 mol % of TosBr was employed, the isolated yield of PVTDO reached 49%, and the obtained PVTDO had a relatively narrow, monomodal molecular weight distribution of 1.8 with an M n of 4100.

show abstract

Addition of sulfonyl iodides to allenes

Cited by 61 publications

References 4 publications

New and Facile Synthesis of Thiosulfonates from Sulfinate/Disulfide/I2 System

New and Facile Synthesis of Thiosulfonates from Sulfinate/Disulfide/I2 System

An Efficient Radical Procedure for the Halogenation and Chalcogenation of B‐Alkylcatecholboranes

Radical ring‐opening polymerization of five‐membered cyclic vinyl sulfone using p‐toluenesulfonyl halides

Contact Info

Product

Resources

About