1967
DOI: 10.1039/j39670001450
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Reaction of trifluoromethylcarbene with cis- and trans-but-2-enes

Abstract: Trifluoromethylcarbene, generated photolytically from 2,2,2-trifluorodiazoethane, reacts essentially stereospecifically with trans-and cis-but-2-enes in the liquid phase, to give dimethyltrifluoromethylcyclopropanes, and olefinic insertion products. In the vapour phase, or in solution in an inert solvent, the degree of stereospecificity of the cyclopropane formation and the yield of insertion products are both lower, consistent with the formation of singlet trifluoromethylcarbene and its decay to a triplet sta… Show more

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Cited by 27 publications
(22 citation statements)
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“…Early studies in this area have entailed the use of trifluoromethylcarbene generated by photolytic decomposition of 2-diazo-1,1,1-trifluorethane (CF 3 CHN 2 ), resulting in a mixture of products. 3 More synthetically useful strategies for olefin trifluoromethylcyclopropanation with this reagent were made available only recently using transition metal catalysis. 4 To date, however, only a few studies have addressed the problem of developing enantioselective variants of these transformations.…”
mentioning
confidence: 99%
“…Early studies in this area have entailed the use of trifluoromethylcarbene generated by photolytic decomposition of 2-diazo-1,1,1-trifluorethane (CF 3 CHN 2 ), resulting in a mixture of products. 3 More synthetically useful strategies for olefin trifluoromethylcyclopropanation with this reagent were made available only recently using transition metal catalysis. 4 To date, however, only a few studies have addressed the problem of developing enantioselective variants of these transformations.…”
mentioning
confidence: 99%
“…In further reports Atherton and Fields reported proof of principle studies on cycloaddition reactions of trifluorodiazoethane with olefins yielding cyclopropanes 12 (9) or pyrazolines (10 and 11) ( Fig. 2), 13 and on insertion reactions providing trifluoroethyl substituted alkanes, silanes, ethers and amines.…”
Section: Early Applicationsmentioning
confidence: 97%
“…The reaction of some enamines, e.g., [28], with dichlorocarbene proceeded in obvious analogy to Eq. (39) (472, 473), whereas the adduct from isobutenyldimethylamine was stable at ambient temperature (474).…”
Section: [27c]mentioning
confidence: 99%