- Process for producing norbornene derivatives
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The invention relates to a process for producing alkyl norbornene derivatives which are useful for radically curable compounds or as precursors of epoxy compounds. The process comprises: reacting an allyl compound (A) having an allyl group represented by the following formula (1), wherein R 1 represents a hydrogen atom, an alkyl group, a hydroxyl alkyl group, or an alkoxy alkyl group, with alkyl-cyclopentadiene dimer (B).
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Page/Page column 11-12
(2008/06/13)
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- Degenerate Thermal Rearrangement of 1,3-Dimethylenecyclopentane. Evidence for Partially Stereospecific Biradical Formation and Closure in 1,3 Shift
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Parolysis of 1,3-bis(dideuteriomethylene)cyclopentane at 370 deg C resulted in a first-order degenerate rearrangement in which the 1,3- and 3,3-shift products were formed in a 2:1 ratio, respectively, indicating the intermediacy of an effectively orthogonal 2,2'-bis(allylmethane) biradical.Pyrolysis of trans- and cis-4,5-dimethyl-1,3-dimethylenecyclopentane (T and C) gave 1,3- and 3,3-shift products with stereochemistry consistent with predominant conrotatory-bevel ring opening to produce the orthogonal diradical directly.Pyrolysis of optically active T gave the 1,3-shift products with 20.8percent inversion of configuration of the migrating carbon indicative of partial stereospecific closure of the biradical.Comparative pyrolysis of optically active T and its bis(dideuteriomethylene) derivative revealed no secondary kinetic deuterium isotop effect, but an alternation in the extent of racemization of starting material and amounts of 1,3- and 3,3-shift products indicates a product-determining isotope effect.These data provide further evidence for an intermediate.
- Gajewski, Joseph J.,Salazar, Jose Del C.
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p. 4145 - 4154
(2007/10/02)
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