Synthesis and Crystal Structures of a Series of Novel Cyclobutanone Derivatives

Abstract

The crystal structures of three novel cyclobutanone derivatives that have been synthesized were determined. I: (C₁₂H₂₀Br₂O): Mr = 340.10, triclinic, P-1, a = 6.036(2), b = 9.756(3), c = 12.613(3) Å, α = 110.761(14), β = 94.037(15), γ = 102.832(12)°, V = 668.1(3) Å³, Z = 2. II: (C₁₃H₂₂Br₂O): Mr = 354.13, monoclinic, P2₁/n, a = 6.139(2), b = 24.948(8), c = 9.548(3) Å, β = 99.756(18)°, V = 1441.2(8) Å³, Z = 4. III: (C₁₅H₂₆Br₂O): Mr = 382.18, monoclinic, P2₁/n, a = 6.602(1), b = 21.044(3), c = 12.074(2) Å, β = 102.304(7)°, V = 1638.9(4) Å³, Z = 4. The cyclobutane rings in I and II are folded with folding angles 10.7(3) and 10.9(4)°, respectively. However, the cyclobutane ring in III is essentially planar with rmsd for the cyclobutanone atoms being 0.0076 Å. The crystal structures of I–III are devoid of any hydrogen bonding interactions.

Graphical Abstract

The synthesis and crystal structures of three novel cyclobutanones have been reported.