1988
DOI: 10.1016/0040-4039(88)85052-4
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Addition-addition-elimination mechanism of 1,3-dipole “dimerization”

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Cited by 18 publications
(6 citation statements)
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“…When the two reagents were combined in equimolar quantities (Table 1, entry 2), the desired coupling product 3b was isolated in 38% yield. Dipole 2 is known to be capable of homo-dimerization [35], and examination of the crude NMR spectra for the reaction revealed the presence of this dimer along with unreacted 1a . We were gratified to find that simply increasing the amount of dipole to 3 equiv amplified the yield to 86%.…”
Section: Resultsmentioning
confidence: 99%
“…When the two reagents were combined in equimolar quantities (Table 1, entry 2), the desired coupling product 3b was isolated in 38% yield. Dipole 2 is known to be capable of homo-dimerization [35], and examination of the crude NMR spectra for the reaction revealed the presence of this dimer along with unreacted 1a . We were gratified to find that simply increasing the amount of dipole to 3 equiv amplified the yield to 86%.…”
Section: Resultsmentioning
confidence: 99%
“…On the other hand, limited examples of UV-promoted photoisomerization and photocyclization of azomethine iminium ions can be found in the literature . Nevertheless, only recently has reactivity of these unique substrates under visible-light photoredox catalytic conditions been demonstrated by Yang and co-workers.…”
mentioning
confidence: 99%
“…1-Alkylidene-3-oxopyrazolidin-1-ium-2-ides (e.g., 2 in eq 1), developed by Dorn and Otto in 1968, are isolable and stable azomethine imines and have been used as 1,3-dipoles in the context of [3 + 2] cycloadditions, giving five-membered nitrogen-containing heterocycles. , Unfortunately, however, these useful 1,3-dipoles have never been engaged in a single-step formation of six-membered rings to date …”
mentioning
confidence: 99%