Cyclic Sulfones and Sulfoxides

Zoller, Uri

doi:10.1002/9780470666357.ch5

Cited by 4 publications

(2 citation statements)

References 349 publications

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“…The formation of the cyclopentene 9 and the monothiodiketone 17 from the trioxide 18 is rationalized by Scheme . SO 2 , which is a better leaving group than SO, would be extruded from 18 initially to give the endo- episulfoxide 19 . Two reactions take place from 19 : (i) the extrusion of SO to furnish the cyclopentene 9 and (ii) the thermal sulfoxide−sulfenate isomerization, which gives the 1,2-oxathietane intermediate 20 to provide the monothiodiketone 17 by a ring opening …”

Section: Resultsmentioning

confidence: 99%

Synthesis and Physical Properties of Sterically Congested Cycloalkenes, 1,2-Di-tert-butyl-3,3,5,5-tetramethylcyclopentene and 1,2-Di-tert-butyl-3,3,6,6-tetramethylcyclohexene

et al. 2000

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Two sterically congested cycloalkenes (9 and 10), congeners of tetra-tert-butylethylene, were synthesized and characterized. Oxidation of the bicyclic 1,3-dithietane 8 with dimethyldioxirane (DMD) gave the endo,endo-disulfoxide 13, thermal isomerization of which to the endo,exo-disulfoxide 15 followed by oxidation with DMD gave the trioxide 18. Heating 18 in refluxing 1,3-dimethyl-2-imidazolidinone furnished 1,2-di-tert-butyl-3,3,5,5-tetramethylcyclopentene (9) in 69% yield by a 2-fold extrusion process. The reaction of the 1,6-diketone dihydrazone 23 with Se(2)Cl(2) gave the selenadiazoline 34 and the 1,3-diselenetane 35. Heating 34 at 115-130 degrees C gave 1,2-di-tert-butyl-3,3,6,6-tetramethylcyclohexene (10), a "didehydro" derivative of tetra-tert-butylethylene, in 43% yield. The C=C bond in 10 is strained in degree comparable to those of most strained alkenes reported so far.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Physical Properties of Sterically Congested Cycloalkenes, 1,2-Di-tert-butyl-3,3,5,5-tetramethylcyclopentene and 1,2-Di-tert-butyl-3,3,6,6-tetramethylcyclohexene

et al. 2000

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“…Thiiranes, thiirane S -oxides, and thiirane S , S -dioxides have attracted the attention of chemists for years. , Interest in these compounds derives largely from two sources. First, these species play key roles in a number of important organic transformations, the most notable being the Ramberg−Bäcklund reaction in which a thiirane S , S -dioxide is formed as an intermediate (eq 1) …”

Section: Introductionmentioning

confidence: 99%

The Formation and Characterization of Three-Membered Ring Carbanions in the Gas Phase: An Experimental and Theoretical Investigation of the Conjugate Bases of Thiirane, ThiiraneS-Oxide, and ThiiraneS,S-Dioxide

et al. 1999

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Deprotonation of thiirane, thiirane S-oxide, and thiirane S,S-dioxide was carried out in the gas phase, and the resulting anions were studied through a series of ion-molecule reactions. The cyclic conjugate bases of thiirane (1b) and thiirane S,S-dioxide (3a) are formed whereas a facile ring opening isomerization to vinyl sulfenate anion (2d, CH 2 dCHSO -) is observed in the thiirane S-oxide case. Vinyl thiolate, the rearrangement product of the conjugate base of thiirane, also is obtained. Proton affinities were determined for 1b, 2d, and 3a. High-level ab initio calculations were also carried out, and the results compared with those obtained from experiment. Orbital arguments are advanced to explain the relative barriers to ring opening for the three anions of interest.

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In Pursuit of Stable, Strained Smallring Sulfur Heterocycles

Zoller

1997

Sulfur reports

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Cyclic Sulfones and Sulfoxides

Cited by 4 publications

References 349 publications

Synthesis and Physical Properties of Sterically Congested Cycloalkenes, 1,2-Di-tert-butyl-3,3,5,5-tetramethylcyclopentene and 1,2-Di-tert-butyl-3,3,6,6-tetramethylcyclohexene

Synthesis and Physical Properties of Sterically Congested Cycloalkenes, 1,2-Di-tert-butyl-3,3,5,5-tetramethylcyclopentene and 1,2-Di-tert-butyl-3,3,6,6-tetramethylcyclohexene

The Formation and Characterization of Three-Membered Ring Carbanions in the Gas Phase: An Experimental and Theoretical Investigation of the Conjugate Bases of Thiirane, ThiiraneS-Oxide, and ThiiraneS,S-Dioxide

In Pursuit of Stable, Strained Smallring Sulfur Heterocycles

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