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Volumn 52, Issue 15, 2013, Pages 4184-4188

Oxidative cyclodimerization after tandem cyclization of dehydrobenzo[14]annulenes induced by alkyllithium

Author keywords

annulenes; density functional calculations; dimerization; lithium; polycycles

Indexed keywords

ALKYLLITHIUMS; ANNULENES; BOND FORMATION; CYCLODIMERIZATION; DOUBLE BONDS; N-BUTYLLITHIUM; POLYCYCLES; TANDEM CYCLIZATION;

EID: 84875846639     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201210233     Document Type: Article
Times cited : (12)

References (34)
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    • Though the reasons for these discrepancies are not understood, one possible interpretation is the relatively low activation energies for the four-membered ring formation (to give 9 from 7 or 10 from 9) compared to those for the five-membered ring formation (to give 8 from 7 or 11 from 9), which result from the proximity effect. Namely, the calculated distance between the bond-forming carbon atoms in 7 is shorter for the four-membered ring formation (2.92Å) than for the five-membered ring formation (3.69Å). In the case of 9, the corresponding distances are 2.82 and 3.24Å, respectively. Though this explanation contradicts Baldwin's rules (i.e., 4-exo-dig vs. 5-endo-dig modes), the steric constraint resulting from the medium-sized rings of 7 and 9 would prevail.
    • Though the reasons for these discrepancies are not understood, one possible interpretation is the relatively low activation energies for the four-membered ring formation (to give 9 from 7 or 10 from 9) compared to those for the five-membered ring formation (to give 8 from 7 or 11 from 9), which result from the proximity effect. Namely, the calculated distance between the bond-forming carbon atoms in 7 is shorter for the four-membered ring formation (2.92Å) than for the five-membered ring formation (3.69Å). In the case of 9, the corresponding distances are 2.82 and 3.24Å, respectively. Though this explanation contradicts Baldwin's rules (i.e., 4-exo-dig vs. 5-endo-dig modes), the steric constraint resulting from the medium-sized rings of 7 and 9 would prevail., J. E. Baldwin, J. Chem. Soc. Chem. Commun. 1976, 734-736.
    • (1976) J. Chem. Soc. Chem. Commun. , pp. 734-736
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.