126690-80-0

Upstream product

• 127-65-1 chloroamine-T 
• 106-99-0 buta-1,3-diene 
• 70-55-3 toluene-4-sulfonamide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 

Downstream Products

• 58567-47-8 (2E)-1N-(p-toluenesulfonamido)-octene 
• 57981-17-6 4-methyl-N-(oct-1-en-3-yl)benzenesulfonamide 

Relevant academic research and scientific papers

Selectivity aspects of the ring opening reaction of 2-alkenyl aziridines by carbon nucleophiles

A series of common organometallic reagents were used in the reaction with an acyclic and a cyclic activated 2-alkenyl aziridines and the selectivity aspects for each aziridine was addressed.

Visible-Light-Driven Nitrogen Radical-Catalyzed [3 + 2] Cyclization of Vinylcyclopropanes and N-Tosyl Vinylaziridines with Alkenes

A visible light photoredox-promoted and nitrogen radical catalyzed [3 + 2] cyclization of vinylcyclopropanes and N-tosyl vinylaziridines with alkenes is developed. Key to the success of this process is the use of the readily tunable hydrazone as a nitrogen radical catalyst. Preliminary mechanism studies suggest that the photogenerated nitrogen radical undergoes reversible radical addition to the vinylcyclopropanes and N-tosyl vinylaziridines to enable their ring-opening C-C and C-N bond cleavage and ensuing cyclization with alkenes.

Diastereoselective Palladium-Catalyzed (3 + 2)-Cycloadditions from Cyclic Imines and Vinyl Aziridines

The synthesis of cyclic imidazolidines via two N-C bond-forming sequences has been developed. The transformation goes through a (3 + 2)-cycloaddition reaction in the presence of catalytic amounts of palladium by combining several vinyl aziridines and cyclic N-sulfonyl imines. Interestingly, the use of LiCl as additive allowed the improvement of diastereoselectivities when less encumbered substrates were used. The imidazolidine derivatives that bear aminal cores are isolated in high yields (15 examples, up to 96% yield) and diastereoselectivities (up to >20:1).

Cobalt-Catalyzed Hydroalkynylation of Vinylaziridines

Transition metal-catalyzed hydroalkynylation reactions are efficient transformations allowing the straightforward formation of functionalized alkynes. Therein, we disclose the cobalt-catalyzed hydroalkynylation of vinylaziridines giving rise to both linea

Visible-Light Photoredox-Catalyzed Formal [5 + 1] Cycloaddition of N-Tosyl Vinylaziridines with Difluoroalkyl Halides

A visible-light photoredox-catalyzed formal [5 + 1] cycloaddition of N-tosyl vinylaziridines with difluoroalkyl halides as unique C1 synthons was developed. The procedure provides an efficient and practical method to synthesize diverse pyridines in moderate to good yields. The reaction underwent a radical-initiated kinetically controlled ring-opening of vinylaziridines and involved a key α,β-unsaturated imine intermediate, followed by an E2 elimination, a 6πelectrocyclization, and defluorinated aromatization.

Diborylalkyllithium Salts Trigger Regioselective Ring Opening of Vinyl Aziridines

gem-Diborylalkanes treated with LiTMP produce α-diborylalkane lithium bases that perform nucleophilic attack on vinyl aziridines with controlled regioselectivity. Preferred SN2 diborylalkylation ring opening reaction on the less sterically hind

Synthesis of indolines: Via a palladium/norbornene-catalyzed reaction of aziridines with aryl iodides

A Pd- and norbornene-catalyzed domino procedure has been developed to synthesize indoline compounds. This reaction provides efficient access to indolines by employing aryl iodides with aziridines as new electrophiles. The transformation is scalable and tolerates a range of functional groups.

The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(I)-Catalyzed Intermolecular Cycloadditions of Vinyl Aziridines and Alkynes

Catalyst-controlled divergent intermolecular cycloadditions of vinylaziridines with alkynes have been developed. By using [Rh(NBD)2]BF4 as the catalyst, a [3 + 2] cycloaddition reaction was achieved with broad substrate scope and high stereoselectivity under mild reaction conditions. Moreover, the chirality of vinylaziridines can be completely transferred to the [3 + 2] cycloadducts. When the catalyst was changed to [Rh(η6-C10H8) (COD)]SbF6, the alternative [5 + 2] cycloadducts were selectively formed under otherwise identical conditions.

Pyridinium hydrobromide perbromide: A versatile catalyst for aziridination of olefins using chloramine-T

Formula presented Pyridinium hydrobromide perbromide (PyHBr3) catalyzes effectively the aziridination of electron-deficient as well as electron-rich olefins using Chloramine-T (N-chloro-N-sodio-p-toluenesulfonamide) as a nitrogen source to afford the corr

CONCOMITANT -SIGMATROPIC REARRANGEMENT OF ALLYLIC SULFILIMINES AND INTRAMOLECULAR N-ALKYLATION. SYNTHESIS OF 2-VINYL SUBSTITUDED CYCLIC AMINES

Allylic phenyl and methyl sulfides bearing a strategically positioned electrophilic center have been shown to undergo concomitant -sigmatropic rearrangement and intramolecular N-alkylation upon oxidative conversion to allylic sulfilimines and treatme