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Volumn 64, Issue 29, 2008, Pages 6909-6919

Selective tandem enyne metathesis for the synthesis of functionalized cycloheptadienes

Author keywords

1,3 Cycloheptadiene; Enyne metathesis; Grubbs' catalyst; Regioselectivity; Ring expansion; Ring synthesis; Site selectivity

Indexed keywords

3 PHENYLBICYCLO[5.2.0]NONA 2,4 DIEN 8 ONE; 4 PHENYLBICYCLO[5.2.0]NONA 2,4 DIEN 8 ONE; ALKADIENE; CYCLOALKENE; CYCLOHEPTADIENE DERIVATIVE; CYCLOHEPTENE; INDENE DERIVATIVE; RUTHENIUM; TETRAHYDROINDENE;

EID: 44949188301     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.027     Document Type: Article
Times cited : (10)

References (27)
  • 14
    • 44949138549 scopus 로고    scopus 로고
    • Kulkarni, A. A. Ph.D. Dissertation, SUNY Buffalo, 2006.
    • Kulkarni, A. A. Ph.D. Dissertation, SUNY Buffalo, 2006.
  • 15
    • 44949171889 scopus 로고    scopus 로고
    • note
    • Critical monomer concentration is another variable. As small molecule synthetic chemists, we make the generalization that lower strain alkenes can be employed in the ring synthesis at higher concentrations without triggering self-ROMP. On the other hand, with strained cycloalkenes, a much lower alkene concentration range must be observed otherwise self-ROMP will become competitive.
  • 21
    • 44949221415 scopus 로고    scopus 로고
    • note
    • The rate law for cycloalkene-alkyne cross-metathesis has not yet been determined. Since cyclopentene is nominally reactive, we liken it to 1-hexene and make the tentative comparison to the mechanism determined by kinetic analysis.
  • 22
    • 44949112584 scopus 로고    scopus 로고
    • note
    • Another possibility is that of diminished reactivity for carbene H due to chelation by the ketone. We considered this unlikely given the results below where the reaction proceeds exclusively through the gem-dimethyl version of carbene H.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.