An extensive study of bromination of cis,trans,trans-1,5,9-cyclododecatriene: product structures and conformations

Abstract

Bromine has been added to cis,trans,trans-1,5,9-cyclododecatriene under various reaction conditions. All expected direct addition products have been isolated, and their structures have been determined by microanalysis, NMR and X-ray crystallography. Advanced NMR techniques were used to determine solution conformations of several of the compounds, enabling comparison with the solid-state conformations obtained by crystallography.

Flame Retardants for Polystyrenes in Commercial Use or Development

“…It is a mixture of three diastereoisomers, with one (the gamma-isomer) comprising 80% of the technical product. The structures have been elucidated by NMR and X-ray crystallography [5]. There are some differences in stability of the isomers [6] and presumably the manufacturers have tried to optimize the process to favor stability at processing temperatures.…”

Structures and Properties of Copper Alkene Complexes. Preorganization Effects and the Binding of Different Isomers of Cyclododecatriene to Copper Triflate

“…43,44 Of the four isomers, ttt-C 12 H 18 is the principal product of the nickel-based cyclotrimerization catalysis. Cyclododecatrienes have numerous uses: 45,46 for example, they can be converted into valuable chemicals such as brominated flame retardants 47 and ingredients for the perfume industry, 48 and they have also been discussed as starting materials for the preparation of the polyamide precursors laurolactam and dodecanedioc acid. [49][50][51] In 1973, Salomon and Kochi 42 described the isolation of adducts of copper(I) triflate with the cct, ctt, and ttt isomers of cyclododecatriene.…”

“…Three of these four trienes (all except the ccc isomer) are prepared by the catalytic cyclotrimerization of butadiene; typically, “naked” nickel serves as the catalyst. , Of the four isomers, ttt-C 12 H 18 is the principal product of the nickel-based cyclotrimerization catalysis. Cyclododecatrienes have numerous uses: , for example, they can be converted into valuable chemicals such as brominated flame retardants and ingredients for the perfume industry, and they have also been discussed as starting materials for the preparation of the polyamide precursors laurolactam and dodecanedioc acid. − …”