Dipole stabilized carbanions in series of cyclic aldonitrones. Part I (1). Aldonitrones metallation and dimerization in LDA and n-Buli solutions Full article
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Heterocyclic Communications
ISSN: 0793-0283 |
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| Output data | Year: 1998, Volume: 4, Number: 3, Pages: 261-270 Pages count : 10 DOI: 10.1515/HC.1998.4.3.261 | ||
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Abstract:
Cyclic aldonitrones 1 (Figure 1) of pyrroline, 3-imidazoline and 2H-imidazole series was shown to be lithiated in LDA and n-BuLi ether solutions yielding dipole-stabilized carbanions 2. In the absence of an "external" electrophile the latter ones react with aldonitrone group of a non-metallated molecule to give dimer products with the structure depending on the initial nitrone structure. Nitrones with non-conjugated aldonitrone group 4a,b yield dinitrones 8a,b (Scheme 2), whereas conjugated nitrones 5a,b yield iminonitrones 10a,b (Schemë 3). Acyclic aldonitrone 7 (PBN) does not undergo lithiation under the same conditions, which is likely to be due to its Z-configuration.
Cite:
Voinov M.A.
, Grigor'ev I.A.
, Volodarsky L.B.
Dipole stabilized carbanions in series of cyclic aldonitrones. Part I (1). Aldonitrones metallation and dimerization in LDA and n-Buli solutions
Heterocyclic Communications. 1998. V.4. N3. P.261-270. DOI: 10.1515/HC.1998.4.3.261 WOS Scopus РИНЦ OpenAlex
Dipole stabilized carbanions in series of cyclic aldonitrones. Part I (1). Aldonitrones metallation and dimerization in LDA and n-Buli solutions
Heterocyclic Communications. 1998. V.4. N3. P.261-270. DOI: 10.1515/HC.1998.4.3.261 WOS Scopus РИНЦ OpenAlex
Dates:
| Published print: | Jan 1, 1998 |
Identifiers:
| Web of science: | WOS:000078255300010 |
| Scopus: | 2-s2.0-0032368875 |
| Elibrary: | 13300188 |
| OpenAlex: | W2320567253 |