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Volumn 30, Issue 7, 2011, Pages 2039-2043

Substituted butenylindium generated by transmetalation of cyclopropylmethylstannane with indium iodide: Synthesis and characterization of monobutenylindium

Author keywords

[No Author keywords available]

Indexed keywords

BULKY SUBSTITUENTS; CARBON-CARBON BOND; CYCLOPROPYL RING; RADICAL COUPLING REACTIONS; STERIC EFFECT; TRANSMETALATION; X RAY STRUCTURAL ANALYSIS;

EID: 79953713417     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200094m     Document Type: Article
Times cited : (9)

References (65)
  • 4
    • 0037253161 scopus 로고    scopus 로고
    • For selected reviews, see
    • For selected reviews, see: Podlech, J.; Maier, T. C. Synthesis 2003, 633-655
    • (2003) Synthesis , pp. 633-655
    • Podlech, J.1    Maier, T.C.2
  • 39
    • 84915362235 scopus 로고
    • A halogen substitution reaction using alkylindium species toward haloalkenes
    • A halogen substitution reaction using alkylindium species toward haloalkenes: Nomura, R.; Miyazaki, S.-i.; Matsuda, H. J. Am. Chem. Soc. 1992, 114, 2738-2740
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 2738-2740
    • Nomura, R.1    Miyazaki S., -i.2    Matsuda, H.3
  • 52
    • 0036090340 scopus 로고    scopus 로고
    • The coupling reaction of holocarbonyls and butenylindium from butenyl Grignard reagent and indium halide was reported
    • The coupling reaction of holocarbonyls and butenylindium from butenyl Grignard reagent and indium halide was reported: Usugi, S.; Tsuritani, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2002, 75, 841-845
    • (2002) Bull. Chem. Soc. Jpn. , vol.75 , pp. 841-845
    • Usugi, S.1    Tsuritani, T.2    Yorimitsu, H.3    Shinokubo, H.4    Oshima, K.5
  • 53
    • 79953703037 scopus 로고    scopus 로고
    • 3 did not give the product 3a at all.
    • 3 did not give the product 3a at all.
  • 55
    • 79953681240 scopus 로고    scopus 로고
    • note
    • 3 = 1:1) in toluene gave monobutenylindium along with a small amount of dibutenylindium. The second transmetalation could be relatively fast because the steric hindrance of substituents of 1b (1c) are smaller than those of 1a and 1d.
  • 56
    • 79953683618 scopus 로고    scopus 로고
    • note
    • The generation of 4d as a single product was observed by NMR spectroscopy.
  • 57
    • 79953689194 scopus 로고    scopus 로고
    • note
    • The data obtained from the measurement was good, and the analysis was completed to optimize the structure. Although some level A alerts still remain, this structure should be justified because of the excellent level of the data and structure refinement.
  • 61
    • 79953685381 scopus 로고    scopus 로고
    • note
    • The reaction of 1b with 2 was examined at 0 °C and gave the products in 86% yield and ratio of 3b / 14b = 37/63. This result indicates that the ratio of 3 / 14 does not depend on a reaction temperature.
  • 65
    • 79953691356 scopus 로고    scopus 로고
    • note
    • 3B) or an open air condition is required in a radical initiation step to facilitate an efficient reaction. On the contrary, because nonsubstituted 13e easily generates a radical species (not fully determined) assisted by oxygen, an additional radical initiator is not required.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.