22332-94-1Relevant academic research and scientific papers
Chlorine versus bromine: Facial selectivity in the Diels-Alder reactions of 5-bromo-1,2,3,4,5-pentachlorocyclopenta-1,3-diene
Burry, Lori C.,Miller, David O.,Burnell, D. Jean
, p. 3825 - 3830 (1998)
Diels-Alder reactions of diene 11 with both electron-poor and electron-rich dienophiles led to approximately 90% addition to the face of 11 syn to the C-5 chlorine. Addition of 4-phenyl-1,2,4-triazoline-3,5-dione was slightly less facially selective. Adduct ratios were obtained by NMR methods; stereochemistry was determined by X-ray crystallography. The results support the view that facial selectivity in Diels-Alder reactions with heteroatom-substituted dienes is mainly controlled by steric, not stereoelectronic, interactions.
SYNTHESIS OF MIXED POLYHALOGENOCYCLOPENTADIENES C5Cl5Br AND C5Cl4Br2
Zaichikova, L. S.,Shestakova, T. G.,Zyk, N. V.,Borisenko, A. A.,Kirpichenok, M. A.,Zefirov, N. S.
, p. 1679 - 1684 (2007/10/02)
A systematic investigation was undertaken into methods for the synthesis of mixed bromochlorocyclopentadienes with 13C NMR spectroscopy as method of analysis.Previously described C5Cl4Br2 compounds were obtained as mixtures of three structural isomers with the halogen atoms at various positions in the cyclopentadiene ring.New preparative methods are proposed for the production of C5Cl5Br.
