Factors influencing the nature of the episulfonium ion in sulfenyl chloride addition to terminal olefins

Mueller, W. H.; Butler, Peter E.

doi:10.1021/ja01010a029

Cited by 132 publications

(33 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The kinetically controlled product composltion was determined by immediate nmr analysis of the reaction mixture. This uz sit11 determination of the adduct isomer ratio is necessary because of the known tendency of many 0-chloros~~lfidcs to isomerize (3)(4)(5).…”

Section: +1mentioning

confidence: 99%

See 1 more Smart Citation

The effect of alkene structure upon the rates and product composition of addition of 4-chlorobenzenesulfenyl chloride

Sçhmid¹,

Dean²,

Garratt³

1976

Can. J. Chem.

View full text Add to dashboard Cite

The rates and products of addition of 4-chlorobenzenesulfenyl chloride to 30 mono- and disubstituted alkenes have been determined in 1,1,2,2-tetrachloroethane at 25 °C. The rates of addition span a range of 106. No correlation with the extended Taft equation was found with the rates of all 30 compounds. The rate ratio kc/kt for addition to nine pairs of isomeric cis-trans alkenes ranges from a low of 3.1 for the 2-butenes to a high of 1.57 × 105 for the 2,2,5,5-tetramethyl-3-hexenes. The rate ratio kc/kt does not always increase regularly with the increasing size of the substituents which suggests that relief of ground state strain is not important in the rate determining transition state. Greater steric hindrance between the electrophile and the trans alkene compared to the cis isomer is proposed to account for the results.

show abstract

Section: +1mentioning

confidence: 99%

“…The addition of arenesulfenyl chlorides to alkenes has been extensively studied by a number of workers (2)(3)(4)(5). As a result of these investigations, a mechanism has been proposed involving a rate determining forination of a thiiranium ion which is then attacked by chloride ion in the product determining step.…”

Section: Introductionmentioning

confidence: 99%

The effect of alkene structure upon the rates and product composition of addition of 4-chlorobenzenesulfenyl chloride

Sçhmid¹,

Dean²,

Garratt³

1976

Can. J. Chem.

View full text Add to dashboard Cite

show abstract

“…The described coupling was also carried out for 4-zert-butyl-l-methoxycyclohexene (2b) and I-methoxycyclopentene (3) under similar conditions using at the final stage allylstannane 18b or trimethylsilyl enol ether of pinacolone (25), respectively. For both reactions the formation of only one of the possible diastereomers was observed.…”

mentioning

confidence: 99%

Diastereoselective synthesis of polyfunctional compounds based on the tandem sequence of threeAd E reactions using cyclic vinyl ethers as first alkene components

et al. 1990

View full text Add to dashboard Cite

show abstract

“…This assignment was based on the following information. (i) All ionic additions of sulfenyl halides to olefins which have been reported to date have led to products in which the alkylthio group and the halogen are trans to each other (1)(2)(3)(4)(5)(6)(7)(8).…”

Section: Resultsmentioning

confidence: 99%

Reaction of ethanesulfenyl chloride with 2-methoxy-5,6-dihydro-2H-pyran

Baldwin¹,

Brown²

1969

Can. J. Chem.

View full text Add to dashboard Cite

The reaction of ethanesulfenyl chloride with 2-methoxy-5,6-dihydro-2H-pyran gives only 413-chloro3a-ethylthio-213-methoxytetrahydropyran. A rationale is presented to explain the observed highly selective reaction.Canadian Journal of Chemistry, 47. 3553 (1969) Introduction Two recent reports from this laboratory (1,2) have described the reaction of alkane (or aralkane) sulfenyl chlorides with 3,4-dihydro-2H-pyran to produce trans-2-chloro-3-alkyl (or aralkyl) thiotetrahydropyran which, in the presence of sodium methoxide in methanol, gave trans-3-alkyl (or aralky1)-2-methoxytetrahydropyrans. A rationale was presented to explain the observed highly selective course of the reaction.The present communication describes the results obtained from the reaction of ethanesulfenyl chloride with 2-methoxy-5,6-dihydro-2H-pyran.

show abstract

Factors influencing the nature of the episulfonium ion in sulfenyl chloride addition to terminal olefins

Cited by 132 publications

References 0 publications

The effect of alkene structure upon the rates and product composition of addition of 4-chlorobenzenesulfenyl chloride

The effect of alkene structure upon the rates and product composition of addition of 4-chlorobenzenesulfenyl chloride

Diastereoselective synthesis of polyfunctional compounds based on the tandem sequence of threeAd E reactions using cyclic vinyl ethers as first alkene components

Reaction of ethanesulfenyl chloride with 2-methoxy-5,6-dihydro-2H-pyran

Contact Info

Product

Resources

About