Selective Oxidation of Sulfides to Sulfoxides with Cetyltrimethylammonium Periodate

Chaudhari, Umesh V.; Deota, Pradeep T.

doi:10.1080/00304948.2012.697729

Cited by 3 publications

(3 citation statements)

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“…Oxidation of 5a using CTAPI in water–methanol (8:2) at 25°C for 45 h following our reported procedure resulted in the formation of diastereomeric sulfoxides ( 6a and 6a' ) in 25.71:74.28 (72% ) (Scheme ). The observed improvement in the diastereomeric ratio in oxidation using CTAPI might be attributed to the steric hindrance between its bulky head group and the equatorial isopropyl group in 5a .…”

Section: Resultsmentioning

confidence: 98%

“…We recently reported selective oxidation of structurally different sulfides to corresponding sulfoxides using hexadecyltrimethylammonium periodate (cetyltrimethylammonium periodate, CTAPI), which has a bulky head group. Such unwieldiness is lacking in conventional oxidants like hydrogen peroxide, sodium metaperiodate, m ‐chloroperbenzoic acid, etc.…”

Section: Resultsmentioning

confidence: 99%

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Steric Considerations on Improving the Diastereomeric Ratio of (+)‐ and (−)‐Neomenthyl Phenyl Sulfoxides Using Bulky‐Headed Oxidant Hexadecyltrimethylammonium Periodate and Assignment of Their Configuration

et al. 2015

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The bulky-headed oxidant hexadecyltrimethylammonium periodate affords the diastereomeric pairs, (Ss)-(+)/(Rs)-(+) and (Ss)-(-)/(Rs)-(-)-neomenthyl phenyl sulfoxides in stereochemically pure states with improved diastereomeric excess (48% diastereomeric excess [de]) as compared to its nonbulky counterpart, sodium metaperiodate (28% de) from respective (+)/(-)-neomenthyl phenyl sulfides. Steric effects involving the head group volume of hexadecyltrimethylammonium periodate is found to play a role in improving the diastereomeric ratio of the products. The two diastereomers can be readily separated by column chromatography. Absolute configuration at the sulfur center in (+)-neomenthyl phenyl sulfoxide was determined by single-crystal X-ray crystallography and found to be Ss. Relative configurations of other sulfoxides were assigned based on the configuration of (+)-neomenthyl phenyl sulfoxide.

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Steric Considerations on Improving the Diastereomeric Ratio of (+)‐ and (−)‐Neomenthyl Phenyl Sulfoxides Using Bulky‐Headed Oxidant Hexadecyltrimethylammonium Periodate and Assignment of Their Configuration

et al. 2015

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“…Typically, sulfoxides can be obtained through the oxidation of the corresponding sulfides, and various oxidants have been successfully exploited in these transformations including H 2 O 2 , NaIO 4 , CrO 3 , KMnO 4 , and others. 4 Although the developed methodologies are simple and effective, there remains considerable room to improve the practical applications and greenness of these protocols. For example, (1) in some cases, O 2 as the green oxidant has great advantages; however, metal catalysts or relatively harsh conditions are always required; (2) it is difficult to control the selectivity of the oxidation and overoxidation of the sulfoxide to the sulfone is unavoidable; (3) due to the use of strong oxidants, sensitive functional groups are incompatible with the oxidation reaction conditions; and (4) excessive amounts of toxic, explosive and hazardous organic or metal oxidants are required, and the onerous separation procedures make purification difficult.…”

Section: Introductionmentioning

confidence: 99%