A Mechanistic Study of the Photochemistry of Carbohydrate<i>p</i>-Toluenesulfonates

Berki, R. J.; Binkley, E. R.; Binkley, Roger W.; Hehemann, David G.; Koholic, Dolores J.; Masnovi, John

doi:10.1080/07328309608005422

Cited by 4 publications

(2 citation statements)

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“…Sulfones are known to suffer carbon−sulfur bond breakage on UV irradiation . This poses the possibility of an alternative mechanism, in which a photocyclization in the presence of adventitious oxygen leads to a tosylphenathrene that is detosylated under the action of UV light.…”

Section: Results An Discussionmentioning

confidence: 99%

Preparation of Phenanthrenes by Photocyclization of Stilbenes Containing a Tosyl Group on the Central Double Bond. A Versatile Approach to the Synthesis of Phenanthrenes and Phenanthrenoids

et al. 2010

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We have developed a useful modification of the classical preparation of phenanthrenes by UV irradiation of stilbenes in the presence of an oxidant. This modification involves the irradiation, in the presence of base, of stilbenes possessing a sulfonyl group linked to the central double bond. We have proved that this protocol can be successfully applied for the synthesis of diverse phenanthrenes and phenanthrenoids.

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Section: Results An Discussionmentioning

confidence: 99%

Preparation of Phenanthrenes by Photocyclization of Stilbenes Containing a Tosyl Group on the Central Double Bond. A Versatile Approach to the Synthesis of Phenanthrenes and Phenanthrenoids

et al. 2010

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“…We recognized that glycals were ideal substrates for this reaction, and as such a range of these carbohydrate derivatives were examined. This would allow access to O -sulfonyl glycosides (in particular 2- O -sulfonyl glycosides), which are a versatile class of synthetic intermediates. − A plethora of glycopyrans and a glycofuran were prepared via this approach, with only a single pair of diastereomers being formed for each substrate ( A2 – A15 ). The reaction was readily scalable, with no appreciable decrease in yield even when using 1 g of NsP.…”

mentioning

confidence: 99%

Bis(arylsulfonyl) Peroxide-Mediated Difunctionalization of Cyclic Enol Ethers

McCourt

Studer

2023

J. Org. Chem.

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A bis(arylsulfonyl) peroxide-mediated 1,2-difunctionalization of cyclic enol ethers is reported. Bis(nosyl) peroxide selectively sulfonylates the 3position of enol ethers, generating an oxocarbenium ion that is trapped by a carboxylic acid nucleophile at the 2-position. The reaction proceeds in a good yield and tolerates a variety of cyclic enol ethers, including glycals as well as various carboxylic acids, which act as the oxocarbeium ion trapping reagents.

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