119752-83-9

Usage

Uses

Used in Palladium-Catalyzed Aminosulfonylation Process:
1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate is used as a sulfur dioxide surrogate in the palladium-catalyzed aminosulfonylation process, enabling the formation of sulfonyl-containing compounds.
Used in Synthesis of Sodium Aryl Sulfinate:
In the reaction with aryl bromides, 1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate is used to synthesize sodium aryl sulfinates, which are valuable intermediates in the synthesis of various organic compounds.
Used in Activation of DMSO:
1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate is used to activate DMSO (dimethyl sulfoxide) for the synthesis of N-aryl-1H-benzo[d]imidazol-1-amine, a compound with potential applications in pharmaceutical and chemical industries.
Used in Activation of o-Vinylanilines:
In the synthesis of 4-aryl quinolines, 1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate is used to activate o-vinylanilines, facilitating the formation of the desired quinolines, which are important building blocks in organic chemistry and drug discovery.

Upstream product

• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 

Downstream Products

• 3112-88-7 Benzyl phenyl sulfone 
• 640723-20-2 fluorosulfonyl fluoride 
• 368-91-2 4-methoxybenzene-1-sulfonyl fluoride 

Relevant academic research and scientific papers

A Convenient Multigram Synthesis of DABSO Using Sodium Sulfite as SO2 Source

A convenient synthesis of DABCO·(SO2)2 (abbreviated as DABSO) is reported. Using a two-chamber setup, sulfur dioxide is generated in one chamber and consumed in the other. This closed system overcomes safety issues related to working

Carbon annulation of ortho-vinylanilines with dimethyl sulfoxide to access 4-aryl quinolines

A palladium-catalyzed annulation of ortho-vinylanilines with dimethyl sulfoxide was developed to access 4-aryl quinolines in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “=CH-” fragment in this transformation. It represents a facile pathway leading to 4-aryl quinolines.

Palladium-catalyzed annulation of 2-(aryldiazenyl) aniline with dimethyl sulfoxide to access N-aryl-1H-benzo[d]imidazol-1-amine

A palladium-catalyzed annulation of 2-(aryldiazenyl) aniline and dimethyl sulfoxide was developed to access N-aryl-1H-benzo[d]imidazol-1-amine in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “[dbnd]CH[sbnd]” fragment during this procedure. It represents a facile pathway leading to benzimidazoles.

Preparation method of aromatic sulfinic acid compound

The invention relates to a preparation method of an aromatic sulfinic acid compound. The preparation method includes the steps of: with Lewis acid as a catalyst, performing a Friedel-Crafts acylation reaction to an aromatic compound as a raw material with 1,4-diazabicyclo[2.2.2]octane (DABSO) in a solvent to generate a corresponding aromatic sulfinic acid compound. Compared with industrial preparation methods for the aromatic sulfinic acid compound in the prior art, the method can synthesize the aromatic sulfinic acid compound in one step, so that experiment operations are simplified and a high-polluting chlorosulfonation step is avoided. The method has mild reaction conditions, wherein the reaction can be carried out under a common normal temperature condition, so that a large amount of energy consumption in production is reduced. The DABSO, compared with gas-phase SO2, is convenient to store and transport, has stable properties at normal temperature and under normal pressure and has safe and simple operations. The raw materials are low in cost and easy to obtain, thus reducing production cost. The method has huge potential in practical use.

Stoichiometric release of SO2 from adducts: Application to the direct synthesis of protected dienes

Abstract The in situ, stoichiometric release of SO2 was studied from DABSO (DABCO adduct with SO2) and DMAP adduct. When involved in cheletropic additions, free SO2 released by this technique proved much more reactive than its adducts. Some examples of applications towards the direct synthesis of protected dienes from allylic alcohols are given.

Combining organometallic reagents, the sulfur dioxide surrogate DABSO, and amines: A One-pot preparation of sulfonamides, amenable to array synthesis

We describe a method for the synthesis of sulfonamides through the combination of an organometallic reagent, a sulfur dioxide equivalent, and an aqueous solution of an amine under oxidative conditions (bleach). This simple reaction protocol avoids the need to employ sulfonyl chloride substrates, thus removing the limitation imposed by the commercial availability of these reagents. The resultant method allows access to new chemical space, and is also tolerant of the polar functional groups needed to impart favorable physiochemical properties required for medicinal chemistry and agrochemistry. The developed chemistry is employed in the synthesis of a targeted 70 compound array, prepared using automated methods. The array achieved a 93% success rate for compounds prepared. Calculated molecular weights, lipophilicities, and polar surface areas are presented, demonstrating the utility of the method for delivering sulfonamides with drug-like properties.

Dimethyl sulfite a potential agent for methylation

The synthesis of methylated ether compounds is an important challenge. A pathway for the synthesis of methyl ethers was investigated using dimethyl sulfite (DMSi). Methylation of 1-octanol was carried out in liquid phase upon different heterogeneous organic and inorganic catalysts at 130°C. Aluminium oxide gave the best result with high conversion and moderate selectivity for methyl 1-octyl ether. Reactions in gas phase at higher temperatures (200°C) were also performed. Methyl 1-octyl ether was obtained in a very high level of selectivity up to 98%. Primary and secondary ethers from unsymmetrical alkyl methyl sulfite were also performed by SO2 extrusion.

DABCO-bis (sulfur dioxide), DABSO, as a convenient source of sulfur dioxide for organic synthesis: Utility in sulfonamide and sulfamide preparation

The charge-transfer complex generated from the combination of DABCO and sulfur dioxide, DABSO, is a bench-stable colorless solid suitable for use in organic synthesis as a replacement for gaseous sulfur dioxide. The complex can be combined with Grignard reagents to form sulfinates, which can then be converted in situ to a series of sulfonamides. Alternatively, reaction with anilines and iodine leads to the formation of a series of sulfamides. Cheletropic addition between DABSO and 2,3-dimethylbutadiene provides the corresponding sulfolene.