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Volumn 69, Issue 22, 2004, Pages 7616-7627

Preparation and regioselective SN2′ reaction of novel gem-difluorinated vinyloxiranes with RLi

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; FLUORINE; SYNTHESIS (CHEMICAL);

EID: 6344260393     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049025x     Document Type: Article
Times cited : (30)

References (88)
  • 17
    • 0032512020 scopus 로고    scopus 로고
    • For chiral building blocks see: (g) Iseki, K. Tetrahedron 1998, 54, 13887.
    • (1998) Tetrahedron , vol.54 , pp. 13887
    • Iseki, K.1
  • 29
    • 6344267905 scopus 로고    scopus 로고
    • Jpn. Kokai Tokkyo Koho JP 02,040,373, Feb. 9, 1990
    • (a) Kaneko, I.; Nakamura, H.; Oharu, K. Jpn. Kokai Tokkyo Koho JP 02,040,373, Feb. 9, 1990.
    • Kaneko, I.1    Nakamura, H.2    Oharu, K.3
  • 69
    • 0000339985 scopus 로고    scopus 로고
    • 300 times stronger interaction with Li was observed for HMPA than THF. See: Reich, H, J.; Kulicke, K. J. J. Am. Chem. Soc. 1996, 118, 273.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 273
    • Reich, H.J.1    Kulicke, K.J.2
  • 71
    • 0034700024 scopus 로고    scopus 로고
    • It is reported that the product regioselectivity by the reaction between RLi and vinyloxiranes was affected by Lewis acidic additives, but in our case, only sluggish results were obtained, possibly due to the ready decomposition of 1b under such circumstance even in the absence of RLi. See: (a) Alexakis, A.; Vrancken, E.; Mangeney, P.; Chemla, F. J. Chem. Soc., Perkin Trans. 1 2000, 3352.
    • (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 3352
    • Alexakis, A.1    Vrancken, E.2    Mangeney, P.3    Chemla, F.4
  • 87
    • 6344293230 scopus 로고    scopus 로고
    • note
    • Semiempirical molecular orbital calculation was performed by MOPAC v 6.10 (PM3) implemented in CAChe Worksystem (Fujitsu) for all the conformers obtained by CONFLEX with the threshold value of 25 kcal, followed by their full optimization by the eigenvector following the minimization (EF) method with the extra keyword "PRECISE", final gradient norm being less than 0.01 kcal/Å.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.