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Article: Density functional theory investigation of the reactivity of LiCH2I and lodomethylzinc phenoxide cyclopropanation reagents with olefins
Title | Density functional theory investigation of the reactivity of LiCH2I and lodomethylzinc phenoxide cyclopropanation reagents with olefins |
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Authors | |
Issue Date | 2002 |
Publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/organometallics |
Citation | Organometallics, 2002, v. 21 n. 26, p. 5901-5910 How to Cite? |
Abstract | We report a systematic density functional theory investigation for the reactions of LiCH2I, IZnCH2I, iodomethylzinc phenoxide (PhOZnCH2I), 2,4,6-F3-PhOZnCH2I, and 2,4,6-Cl3PhOZnCH2I with CH2CH2, trans-CH3CHCHCH3, and PhCHCH2. All of the reactions examined displayed similar concerted mechanisms for the cyclopropanation of these reagents. The zinc carbenoids had similar barriers for the cyclopropanation reaction (in the 17-21 kcal/mol range), while the LiCH2I carbenoid had a much lower barrier for the cyclopropanation reactions (in the 6-7 kcal/mol range). The properties and chemical reactivity of the carbenoids investigated here were compared to each other and to recent results for the isodiiodomethane (CH2I-I) species. |
Persistent Identifier | http://hdl.handle.net/10722/167411 |
ISSN | 2023 Impact Factor: 2.5 2023 SCImago Journal Rankings: 0.654 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
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dc.contributor.author | Wang, D | en_US |
dc.contributor.author | Phillips, DL | en_US |
dc.contributor.author | Fang, WH | en_US |
dc.date.accessioned | 2012-10-08T03:06:40Z | - |
dc.date.available | 2012-10-08T03:06:40Z | - |
dc.date.issued | 2002 | en_US |
dc.identifier.citation | Organometallics, 2002, v. 21 n. 26, p. 5901-5910 | en_US |
dc.identifier.issn | 0276-7333 | en_US |
dc.identifier.uri | http://hdl.handle.net/10722/167411 | - |
dc.description.abstract | We report a systematic density functional theory investigation for the reactions of LiCH2I, IZnCH2I, iodomethylzinc phenoxide (PhOZnCH2I), 2,4,6-F3-PhOZnCH2I, and 2,4,6-Cl3PhOZnCH2I with CH2CH2, trans-CH3CHCHCH3, and PhCHCH2. All of the reactions examined displayed similar concerted mechanisms for the cyclopropanation of these reagents. The zinc carbenoids had similar barriers for the cyclopropanation reaction (in the 17-21 kcal/mol range), while the LiCH2I carbenoid had a much lower barrier for the cyclopropanation reactions (in the 6-7 kcal/mol range). The properties and chemical reactivity of the carbenoids investigated here were compared to each other and to recent results for the isodiiodomethane (CH2I-I) species. | en_US |
dc.language | eng | en_US |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/organometallics | en_US |
dc.relation.ispartof | Organometallics | en_US |
dc.title | Density functional theory investigation of the reactivity of LiCH2I and lodomethylzinc phenoxide cyclopropanation reagents with olefins | en_US |
dc.type | Article | en_US |
dc.identifier.email | Phillips, DL:phillips@hku.hk | en_US |
dc.identifier.authority | Phillips, DL=rp00770 | en_US |
dc.description.nature | link_to_subscribed_fulltext | en_US |
dc.identifier.doi | 10.1021/om020679a | en_US |
dc.identifier.scopus | eid_2-s2.0-0013350854 | en_US |
dc.identifier.hkuros | 77119 | - |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-0013350854&selection=ref&src=s&origin=recordpage | en_US |
dc.identifier.volume | 21 | en_US |
dc.identifier.issue | 26 | en_US |
dc.identifier.spage | 5901 | en_US |
dc.identifier.epage | 5910 | en_US |
dc.identifier.isi | WOS:000179932500026 | - |
dc.publisher.place | United States | en_US |
dc.identifier.scopusauthorid | Wang, D=7407071795 | en_US |
dc.identifier.scopusauthorid | Phillips, DL=7404519365 | en_US |
dc.identifier.scopusauthorid | Fang, WH=7202236871 | en_US |
dc.identifier.issnl | 0276-7333 | - |