Synthesis 2007(12): 1833-1836  
DOI: 10.1055/s-2007-983711
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Higher-Order Cycloaddition Reactions of 8,8-Dicyanoheptafulvene with Dienes

Vijay Nair*a,b, K. Gopalakrishnan Abhilasha, Akkattu T. Bijua, Eringathodi Sureshc
a Organic Chemistry Section, Regional Research Laboratory (CSIR), Trivandrum 695019, India
Fax: +91(471)2491712; e-Mail: vijaynair_2001@yahoo.com;
b Jawaharlal Nehru Centre for Advanced Scientific Research, Bangalore 560064, India
c Central Salt and Marine Chemicals Research Institute (CSIR), Bhavnagar 364002, India
Further Information

Publication History

Received 13 March 2007
Publication Date:
08 June 2007 (online)

Abstract

The cycloaddition reactions of 8,8-dicyanoheptafulvene with electron-rich dienes afforded the higher order cycloaddition products in excellent yields. With cyclic dienes as well as dimeth­oxybutadiene the [8+2] adducts were obtained exclusively. With methyl- and dimethylbutadienes the [6+4] adducts were the only products isolated.

    References

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7

Crystal data for 3a: empirical formula C32H32N4, formula weight 472.62, triclinic, space group P-1, a = 7.123(2) Å, b = 8.306(3) Å, c = 11.506(4) Å, α = 87.363(6)°, β = 81.053(7)°, γ = 83.939(6)°, V = 668.4(4) Å3, Z = 1, D calcd = 1.174 Mg/m3, λ = 0.71073 Å, absorption coefficient = 0.070 mm-1, F(000) = 252, T = 293(2) K, crystal size = 0.22 × 0.10 × 0.06 mm. CCDC 639690 contains the supplementary crystallographic data for this compound.

8

Crystal data for 3c: empirical formula C17H16N2O, formula weight 264.32, monoclinic, space group P21/n, a = 8.4450(12) Å, b = 13.0730(18) Å, c = 12.8118(18) Å, α = 90°, β = 99.069(3)°, γ = 90°, V = 1394.6(3) Å3, Z = 4, D calcd = 1.259 Mg/m3, λ = 0.71073 Å, absorption coefficient = 0.080 mm-1, F(000) = 560, T = 273(2) K, crystal size = 0.30 × 0.20 × 0.12 mm. CCDC 639691 contains the supplementary crystallographic data for this compound.

9

Crystal data for 3e: empirical formula C16H16N2O2, formula weight 268.31, monoclinic, space group = P21/n, a = 8.0664(8) Å, b = 14.2902(15) Å, c = 13.3056(14) Å, α = 90°, β = 103.564(2)°, γ = 90°, V = 1491.0(3) Å3, Z = 4, D calcd = 1.195 Mg/m3, λ = 0.71073 Å, absorption coefficient = 0.080 mm-1, F(000) = 568, T = 296(2) K, crystal size = 0.34 × 0.28 × 0.22 mm. CCDC 639692 contains the supplementary crystallographic data for this compound.