Chemistry of benzenesulfinyl azides. Reactions with sulfoxides

Maricich, Tom J.; Hoffman, Virgil L.

doi:10.1021/ja00832a026

Cited by 42 publications

(11 citation statements)

References 10 publications

(13 reference statements)

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“…Unfortunately, the method calls for the use of the free base of hydroxylamine, which is unstable, unsafe, and difficult to handle. Another example, published by Maricich and Hoffman, involved generation of the sulfinyl azide 4a by reaction of 2a (R = Ph) with NaN 3 at low temperature (Scheme ). The intermediate 4a proved explosive when warmed neat; however, its slow decomposition in the presence of water afforded 1a in 20% yield.…”

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confidence: 99%

tert-Butylsulfonamide. A New Nitrogen Source for Catalytic Aminohydroxylation and Aziridination of Olefins

1999

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[reaction: see text] The N-chloramine salt of tert-butylsulfonamide has been shown to be an efficient nitrogen source and the terminal oxidant for catalytic aminohydroxylation and aziridination of olefins, resembling closely Chloramine-T by its behavior in these catalytic reactions. The sulfonyl-nitrogen bond in the product or its derivatives is easily cleaved under mild acidic conditions, allowing for facile liberation of the amino group.

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confidence: 99%

tert-Butylsulfonamide. A New Nitrogen Source for Catalytic Aminohydroxylation and Aziridination of Olefins

1999

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“…In this case, too, the operation of an apical-equatorial substitution mechanism with the formation of the transient sulfurane 247 was proposed. A similar mechanism was advanced by Maricich and Hoffman (136) to explain retention at sulfur in the reaction of a sulfoxide with p-toluenesulfinylnitrene leading also to a sulfmide via…”

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confidence: 57%

Chiral Organosulfur Compounds

Mikołajczyk

Drabowicz

1982

Topics in Stereochemistry

113

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“…We hypothesised that the use of a sulfinylamine bearing a suitable leaving group on nitrogen would, after addition of a carbon nucleophile, lead to rare S‐electrophilic sulfinyl nitrene intermediates. [30] It was planned that these species would react more efficiently with organolithium and Grignard reagents. We found that the O ‐aryl‐ N ‐sulfinylhydroxylamine BiPhONSO ( 16 ) combines good stability and a convenient solid form with excellent reactivity.…”

Section: Synthesis Of Sulfur(vi) Compoundsmentioning

confidence: 99%

Rediscovering Sulfinylamines as Reagents for Organic Synthesis

Davies

Willis

2021

Chemistry A European J

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Sulfinylamines (RÀ N=S=O), monoaza analogues of sulfur dioxide, have been known for well over a century, and their reactivity as sulfur electrophiles and in Diels-Alder reactions is well-established. However, they have only rarely been used in organic synthesis in recent decades despite the increasing prominence of compounds containing N=S=O functionality, such as sulfoximines and sulfonimidamides. This Minireview aims to bring wider visibility to the unique chemistry enabled by this class of compounds. We focus on advances from the last 10 years, including the first examples of their use in the one-pot syntheses of sulfoximines and sulfonimidamides. Also covered are the reactions of sulfinylamines with carbon-centred radicals, their use for formation of heterocycles through cycloadditions, and catalytic enantioselective allylic oxidation of alkenes via a hetero-ene reaction. These examples highlight the different reactivity modes of sulfinylamines and their underappreciated potential for forming molecules which contain high-or low-valent sulfur, or even no sulfur at all.

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Chemistry of benzenesulfinyl azides. Reactions with sulfoxides

Cited by 42 publications

References 10 publications

tert-Butylsulfonamide. A New Nitrogen Source for Catalytic Aminohydroxylation and Aziridination of Olefins

tert-Butylsulfonamide. A New Nitrogen Source for Catalytic Aminohydroxylation and Aziridination of Olefins

Chiral Organosulfur Compounds

Rediscovering Sulfinylamines as Reagents for Organic Synthesis

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