Synthesis and crystal structure of 2,6‐dibromo‐3,7‐dimethyl‐1H,5H‐pyrazolo[1,2‐a]Pyrazole‐1,5‐dione

Blenderman, Walter G.; Carroll, Patrick J.; Joullié, Madeleine M.; Ulatowski, Terrance G.; Nemeroff, Norman H.

doi:10.1002/prac.19863280428

Cited by 5 publications

(1 citation statement)

References 11 publications

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“…The exact reason for this deformation of 3 is unclear, but it is a common characteristic of previously reported syn - and anti -dioxobimanes. Thus, out of the 12 syn - and 6 anti -dioxobimanes currently found in the CSD, which are simply bicyclic, half of the syn -bimanes and a third of the anti -bimanes are bent, whereas the rest are planar. ,,− The CSD contains 11 additional syn -dioxobimanes, but these exhibit a fused tricyclic framework, wherein the two pyrazolinone rings are mutually bridged through their β-olefinic positions by an aliphatic or heteroaliphatic chain. All of these tricyclic bimanes are bent about their N–N bonds, with most being strongly deformed.…”

Section: Resultsmentioning

confidence: 99%

Thioxobimanes

Das,

Roy,

Nandi

et al. 2023

J. Org. Chem.

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Dioxobimanes, colloquially known as bimanes, are a well-established family of N-heterobicyclic compounds that share a characteristic core structure, 1,5-diazabicyclo[3.3.0]octadienedione, bearing two endocyclic carbonyl groups. By sequentially thionating these carbonyls in the syn and anti isomers of the known (Me,Me)dioxobimane, we were able to synthesize a series of thioxobimanes, representing the first heavy-chalcogenide bimane variants. These new compounds were extensively characterized spectroscopically and crystallographically, and their aromaticity was probed computationally. Their potential role as ligands for transition metals was demonstrated by synthesizing a representative gold(I)−thioxobimane complex.

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