16177-47-2Relevant academic research and scientific papers
Facial Selectivity in the Diels-Alder Reactions of 5-Chloro-, 5-Bromo-, and 5-Iodo-l,3-cyclopentadiene and Derivatives
Wellman, Mark A.,Burry, Lori C.,Letourneau, Johnathon E.,Bridson, John N.,Miller, David O.,Jean Burnell
, p. 939 - 946 (2007/10/03)
A variety of dienophiles was used to assess the facial selectivity of Diels-Alder reactions in a series of 1,3-cyclopentadiene derivatives (1-3, 6-10) in which chlorine, bromine, and iodine were planenonsymmetric atoms pitted against hydrogen or methyl at C-5. The results were rationalized in terms of the major factor controlling the facial selectivity being related to steric hindrance between the diene and the dienophile. Selectivity did not correlate with reactivity. Facial selectivity in the reactions with 4-phenyl-l,2,4-triazoline-3,5-dione as the dienophile was also influenced by a second significant factor, postulated to be filled-orbital repulsion with the halogen substituent.
Substituted polyhalogenated cyclopentadienes
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, (2008/06/13)
Compounds of the formula SPC1 Wherein Y is independently selected from the group consisting of methyl, hydrogen and a halogen of atomic weight between 35 and 80 with at least four of the Y substituents being said halogen; each R is independently selected from the group consisting of alkyl having at least one and a maximum of 12 carbon atoms, alkenyl having at least 2 and a maximum of 5 carbon atoms, alkoxyalkyl having at least 2 and a maximum of 6 carbon atoms and cycloalkyl having at least 5 and a maximum of 6 carbon atoms, and n is one of the integers one or two. These compounds possess insecticidal activity and are valuable intermediates for the preparation of insecticides having low mammalian toxicity.
