13466-55-2Relevant academic research and scientific papers
1,3-Dipolar Cycloaddition of 1-Methyl-3-oxidopyridinium and Sulfonylethenes. A Synthesis of 2-Tropanols and Monofluorinated 2-Tropanol
Takahashi, Tamiko,Hagi, Toru,Kitano, Kazuyoshi,Takeuchi, Yoshio,Koizumi, Toru
, p. 593 - 596 (2021/10/14)
2α- and 2β-Tropanols were synthesized by 1,3-dipolar cycloaddition of phenyl vinyl sulfone and 1-methyl-3-oxidopyridinium regio- and stereoselectively.The method was extended to a preparation of 6α-fluoro-2β-tropanol from 1-(benzenesulfonyl)-1-fluoroethene.
Solvolytic Rearrangements of Azabicyclic Compounds. Part 2. Kinetics
Bastable, John W.,Dunkin, Ian R.,Hobson, John D.
, p. 1346 - 1351 (2007/10/02)
Rates of solvolysis in aqueous ethanol and aqueous dioxan of three 2-exo-chloroazabicycloalkanes have been studied and first-order rare constants are derived and compared with published values for analogous compounds.Anchimeric assistance by the bridge N-atom is evidently not important in the rate-controlling step in these rearrangements, though it may occur to a minor extent in the case of 2-exo-chloro-7-methyl-7-azanorbornane.Solvolytic results for tropan-2β-yl toluene-p-sulphonate in aqueous ethanol and aqueous acetone mixtures are also reported and compared with literature data for the carbobicyclic and oxabicyclic analogues.
REDUCTIVE TRANSFORMATION OF A HYDROXYIODOKETONE OF 8-AZABICYCLOOCTANE INTO 7-AZABICYCLOHEPTANE WITH LITHIUM ALUMINIUM HYDRIDE
Sarel, Shalom,Dykman, Edmund
, p. 719 - 734 (2007/10/02)
1α,4β-Diodo-2α-acetoxytropan-3-one (2) and 1α-iodo-2α-acetoxytropan-3-one (3), which comprise 64percent of products emerging from the lead tetraacetate oxidation of tropan-3α-ol in presence of iodine, were subjected to lithium aluminium hydride reduction.The expected 2.3-dihydroxytropane was not obtained.Instead, a diol which was not prone to periodate oxidation, containing one primary and one secondary alkoholic groups was obtained.It was assigned the 1-hydroxymethyl-2α-hydroxy-7-methyl-7-azabicycloheptane structure (8), on the basis of spectroscopic evidences (ir, nmr and mass spectrometry) and some chemical transformations heptane (12)>.The reaction is understood as an initial β-elimination process, triggered by the delivery of hydride ion to the carbonyl function in the sequence 3 21 22, yielding a highly reactive enolate aldehyde (22) which is prone to an immediate internal aldol condensation (22) (23) (24), affording the observed diol (8) on further reduction of the a aldehydic group by LiALH4.The reductive deiodination of (3) into 2α-acetoxytropine (2b) or into 2α-hydroxytropan-3-one (25) was smoothly achieved by means of hydrogenation over Raney Nickel on mild basic conditions.
