메뉴 건너뛰기




Volumn 74, Issue 20, 2009, Pages 7947-7950

Halonium ion-assisted deiodination of styrene-based vicinal iodohydrins followed by rearrangement through phenyl migration

Author keywords

[No Author keywords available]

Indexed keywords

ACID ACTIVATION; CHEMICAL EQUATIONS; DEIODINATION; GOOD YIELD; HALONIUM; ORGANIC LAYERS;

EID: 70349866014     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9013707     Document Type: Article
Times cited : (8)

References (30)
  • 11
    • 70349881364 scopus 로고    scopus 로고
    • note
    • At room temperature, 2-3% of acetophenone was formed along with the phenyl acetaldehyde.
  • 12
    • 70349868938 scopus 로고    scopus 로고
    • note
    • Given that there is only 0.43 mol total of Br in this reagent per mole of iodine in substrate taken, all of the I from the substrate cannot be in the form of IBr in this case.
  • 13
    • 70349883551 scopus 로고    scopus 로고
    • note
    • GC-MS of the product mixtures of the reactions in Table 1 indicated traces of epoxide which may have formed as an impurity, presumably via a competing pathway.
  • 20
    • 33847583651 scopus 로고
    • and references cited therein
    • (f) Tiffeneau, M. Bull. Soc. Chim. Fr. 1908, 1, 1205 and references cited therein.
    • (1908) Bull. Soc. Chim. Fr. , vol.1 , pp. 1205
    • Tiffeneau, M.1
  • 21
    • 37049141789 scopus 로고
    • + resulting in a strongly electrophilic bromonium ion
    • + resulting in a strongly electrophilic bromonium ion: Gilow, H. M.; Ridd, J. H. J. Chem. Soc., Perkin Trans. 2 1973, 1321.
    • (1973) J. Chem. Soc., Perkin Trans. 2 , pp. 1321
    • Gilow, H.M.1    Ridd, J.H.2
  • 26
    • 0000189651 scopus 로고
    • All geometries were fully optimized with the Becke3 Lee-Yang-Parr (B3LYP) method
    • All geometries were fully optimized with the Becke3 Lee-Yang-Parr (B3LYP) method: Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648
    • Becke, A.D.1
  • 28
    • 33745770836 scopus 로고
    • The reactions used the pseudopotential basis set LACVP*: Vibrational analyses were also performed to confirm the local minima. All calculations were performed using Spartan'06 (Wavefunction, Inc.: Irvine, CA) quantum chemical program (Ganguly, B.; Kesharwani, M. K.; Agrawal, M. K.; Ghosh, P. K. Unpublished results)
    • The reactions used the pseudopotential basis set LACVP*: Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270. Vibrational analyses were also performed to confirm the local minima. All calculations were performed using Spartan'06 (Wavefunction, Inc.: Irvine, CA) quantum chemical program (Ganguly, B.; Kesharwani, M. K.; Agrawal, M. K.; Ghosh, P. K. Unpublished results).
    • (1985) J. Chem. Phys. , vol.82 , pp. 270
    • Hay, P.J.1    Wadt, W.R.2
  • 29
    • 70349852307 scopus 로고    scopus 로고
    • note
    • 11
  • 30
    • 60949107951 scopus 로고    scopus 로고
    • All the iodohydrins employed in the present work were synthesized and isolated following the literature procedure
    • All the iodohydrins employed in the present work were synthesized and isolated following the literature procedure: Agrawal, M. K.; Adimurthy, S.; Ganguly, B.; Ghosh, P. K. Tetrahedron 2009, 65, 2791.
    • (2009) Tetrahedron , vol.65 , pp. 2791
    • Agrawal, M.K.1    Adimurthy, S.2    Ganguly, B.3    Ghosh, P.K.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.