Preparation of pure optically active (3s)‐ and (4s)‐tert‐butylcyclohexenes

Ab initio absorption spectra of 3-tert-butylcyclohexene

“…The only available experimental data concerning optical spectra are the measurements of the optical rotation [6,3]. The experimental values are between 1.9 and 3.5 eV, meaning within the absorption gap.…”

“…Chiral carbon compounds are of interest in pharmacy and in biological processes for many years. In particular, the conformationally flexible alkene 3-tert-butylcyclohexene has been studied in the past, [1][2][3] since it is, e.g., a detectable end product after a hydrolysis in the rabbit liver [4]. It plays also a major role in the preparation of epoxides as a basis for the formation of halohydrins [1].…”

“…3-tert-butylcyclohexene (C10H18) is the only 3-alkylcyclohexene with optical activity [3]. Moreover, it is the one with the most extended alkyl group.…”

“…A possible confirmation of the existence of 3-tert-butylcyclohexene as a reaction product is the measurement of its optical rotation. The optical rotation was detected not only for the commonly used sodium D line, but also for various wavelengths of light by Bellucci et al [6] and by Sadozai et al [3] However, an ab-initio calculation of the optical rotation has lead to a qualitative agreement but with the wrong sign [7]. The molecule is conformationally flexible and both conformers are close in energy.…”

First-principles investigation of the vibrational properties of 3-tert-butylcyclohexene

“…In particular, the study of chiral carbonbased molecules has grown in the last years. One example is the conformationally flexible alkene 3-tert-butylcyclohexene [1][2][3]. 3-tert-butylcyclohexene is a detectable end product in the rabbit liver after hydrolysis [4].…”