1982
DOI: 10.1021/ja00377a022
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Cycloaddition reactions of allenes with N-phenylmaleimide. A two-step, diradical-intermediate process

Abstract: The stereoselectivities, chemoselectivities, relative reactivities, and kinetic isotope effects have been determined in the cycloaddition reactions of substituted alienes with iV-phenylmaleimide. The comparison of these results with those derived from the studies of the cycloaddition of 1,1 -dichloro-2,2-difluoroethene and the radical-chain addition of benzenethiol to alienes strongly indicates that the cycloadditions with TV-phenylmaleimide occur via a two-step, diradical-intermediate process. The stereochemi… Show more

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Cited by 14 publications
(10 citation statements)
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“…26 In these experiments, four expected cycloadducts were obtained along with ene products. The chemoselectivities, stereospecificities, and relative reactivities have been explained via two-step diradical-intermediate processes.…”
Section: Dimerization and Intermolecular [2+2] Cycloadditions Of Allementioning
confidence: 93%
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“…26 In these experiments, four expected cycloadducts were obtained along with ene products. The chemoselectivities, stereospecificities, and relative reactivities have been explained via two-step diradical-intermediate processes.…”
Section: Dimerization and Intermolecular [2+2] Cycloadditions Of Allementioning
confidence: 93%
“…The above criteria have been applied to the results derived from the cycloaddition reactions of substituted allenes with N-phenylmaleimide. 26 In these experiments, four expected cycloadducts were obtained along with ene products. The chemoselectivities, stereospecificities, and relative reactivities have been explained via two-step diradical-intermediate processes.…”
Section: Dimerization and Intermolecular [2+2] Cycloadditions Of Alle...mentioning
confidence: 93%
See 2 more Smart Citations
“…(7.52), 4 (10.60), C (vermutlich 1-Dimeres, 26.11). (26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39)(40)(41)(42), 4 (55)(56)(57)(58)(59)(60)(61)(62)(63)(64)(65)(66)(67).…”
Section: Das Verwendete Kaufliche Allenmentioning
confidence: 99%