Stereoselective H₂O eliminations in 3‐ and 4‐arcylcyclohexanols under electron impact

Abstract

The elimination of H,O from the molecular ions of trans-4-and trans-3-arylcyclohexanols takes place to a greater extent than in the corresponding cis isomers. The remarkable differences in abundance, taken together with substituent effects and the results of deuterium labelling, show that configuration is retained in the molecular ions which undergo the elimination, and that this process is a cis-l,4 and cis-l,3 elimination in the trans-4and trans-3-arylcyclohexanols, respectively. Possible mechanisms for the elimination in the cis isomers are discussed.

Collision-induced dissociation study of stereospecific elimination processes of stereoisomeric phenylcyclohexanols and their derivatives upon electron ionization

“…7,8 This Ðnding is consistent with the large distance between that H-atom and the oxygen in the cis-isomers, which does not allow a 1,4-elimination involving the bezylic position. The major origin of the hydrogen atom abstracted in the course of this elimination has not been established in that study.…”

The First Centrohexaindane Bearing Twelve Functional Groups at Its Outer Molecular Periphery and Related Lower Veratrole‐Derived Centropolyindanes

“…Similarly rapid, and highly stereospecific, loss of water is known for other preoriented bridgehead-hydroxylated centropolyindanes and simpler cyclic alcohols. [32][33][34] Attempts to isolate the triol 18 by chromatography failed; nevertheless, partial separation of the mixture by flash chromatography prior to the next synthesis step proved to be favorable.…”

The substituent effect in the fragmentation of phenylcyclohexanols

“…The publication of a study on the stereochemical aspects of this fragmentation in 4-and 3-phenylcycl~hexanols~ prompted us to record our conclusions, which differ from those reported in the abovementioned paper. Our work concerns a series (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13) of trans-4-and 2phenylcyclohexanols and some deuterated analogues (1-4-d,, 2-4-d1, 7-4-dl).…”