Certain cinnamonitriles react with 2-methoxyfuran to produce a new phenylcyclopropane product

Heterocycles

Volumn 68, Issue 2, 2006, Pages 395-400

  Itoh, Kuniaki ^a   Iwata, Shin ^a   Kishimoto, Shigehisa ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646687544     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-10656     Document Type: Article

References (19)

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11. 4: C, 71.31; H, 6.34. Found: C, 71.36; H, 6.16.
12. -3, R= 0.128 (Rw=01082.) for 3533 refection data point with I>1σ and 1996 variables. CCDC No.291612.
13. The structure of 2-cyano-3-phenylcyclopropane (3d) was determined by the X-Ray crystallo graphic analysis. Itoh K., and Iwat S. CCDC No. 1267/1382. Z. Kristallogr. N.C.S. 219 (2004) 455
14. R. Huigen indicated the formation of a cyclopropane via the zwitterionic intermediate at the reactions of the furans and the ethylene derivatives. We calculated the potential energy for the transition state of Figure 2 using the PM3 method. It is the appropriate value: 36.9 kcal/mol. G. U-Desmaison, G. Mloston, and R. Huigen, Tetrahedron Lett., 1994, 35, 4977; G. Mloston and R. Huisgen, J. Heterocycl. Chem., 1994, 31, 1279.
15. The regioselectivity for the reaction can be predicted from the calculated orbital coefficient of the olefinic carbon atoms and the furan atoms. Furthermore, the secondary orbital interactions found by a PM3 calculation using Spartan v. 4.0.1, led us to expect a stereoselective outcome. {A figure is presented} The calculated orbital coefficients of the olefinic carbon atoms
16. In general, the MM3 strain energy of the trans product is smaller than that of the cis isomer. However, in the case of β-phenylsulfonylcyanostyrene, the energy of the trans product is larger than that of the cis isomer. (Δ 1.09 kcal/mol) The MM3 strain energy was calculated using CAChe ver. 4.4 (Oxford Molecular Limited).
17. The distance is calculated by a PM3 method using Spartan v. 4.0.1.
18. Molecular Structure Corporation (1994), teXsan, Single Crystal Structure Analysis Software, Ver.1.7, MSC 3200, Research Forest Drive. The Woodlands TX77381, USA.
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