Tetrahedron p. 4321 - 4330 (1985)
Update date:2022-08-11
Topics:
Lightner, David A.
Pak, Chwang Siek
Crist, B. Vincent
Rodgers, Stephen L.
Givens, John W.
(1S,5S)-exo-2(R)-Methylbicyclo<3.1.0>hexan-3-one (1) and (1S,5S)-endo-2(S)-methylbicyclo<3.1.0>hexan-3-one (2) were synthesized and their circular dichroism (CD) spectra run.Conformational analysis based on molecular mechanics calculations and Karplus equation analyses of vicinal H/H NMR coupling constants indicate boat-like sofa conformations for both 1 and 2, with very little ring distortion from the symmetry of the parent bicyclo<3.1.0>hexan-3-one.The lone dissymmetric ψ-axial and ψ-equatorial methyl groups of 1 and 2, respectively, are both octant consignate.The natural product analogs of 1 and 2, (-)-3-isothujone (3) and (+)-3-thujone (4) were prepared and examined similarly.Their α-methyl perturbers dominate the CD n-?* Cotton effects.
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