1590-21-2Relevant articles and documents
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Dauben,Tilles
, p. 785,787 (1950)
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Electrophilic Substitution in Naphthalenes: Cyclisation of Naphthylbutanols to Tetrahydrophenanthrene
Jackson, Anthony H.,Shannon, Patrick V. R.,Taylor, Paul W.
, p. 286 - 297 (1981)
Both 4-(1-naphthyl)butanol and 4-(2-naphthyl)butanol cyclised in refluxing boron trifluoride-ether to give 1,2,3,4-tetrahydrophenanthrene.By use of the corresponding 1,1-dideuteriobutanol derivatives and analysis of the products by 220 MHz 1H n.m.r. spectroscopy it has been demonstrated that the 1-naphthylbutanol cyclises by two distinct pathways, (a) by direct attack (84percent) at the 2-position, and (b) by ipso-attack (16percent) at the 1-position of the naphthalene nucleus, followed by rearrangement.The 2-naphthylbutanol cyclises exclusively by direct substitution at the 1-position.With 4-(4-methoxy-1-naphthyl)-1,1-dideuteriobutanol on the other hand the proportion of ipso-substitution rises to 71 percent as shown by the 360 MHz 1H n.m.r. spectra of the resulting mixture of tetrahydrophenanthrenes.
Transition Metal-Free Alkyne-Aldehyde Reductive C?C Coupling trough Cascade Borylation/Olefin Isomerization
Khan, Imran,Luo, Zhibin,Xu, Yin,Xie, Jimin,Zhu, Weihua,Liu, Bin
, (2020/05/04)
A direct approach to γ-keto esters through cascade alkyne-aldehyde reductive C?C coupling of propargyl esters and aromatic aldehydes under transition-metal-free (TM-free) fashion was developed. Compared with multistep processes, this procedure provides a
Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters to synthesize γ-ketone esters
Lai, Luhao,Li, A-Ni,Zhou, Jiawei,Guo, Yarong,Lin, Li,Chen, Wei,Wang, Rui
, p. 2185 - 2190 (2017/03/17)
This work concerns the Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters with TMEDA as an additive. The isomerization proceeded under mild conditions and afforded γ-keto esters in high yield (up to 96%) within 2 h. Both (Z)- and (E)-γ-hydroxy-α,β-alkenoic esters were tolerated under the reaction conditions. This transformation involves the in situ formation of a dienolate intermediate from the easily accessible γ-hydroxy-α,β-alkenoic ester. The in situ generated dienolate can react with benzaldehyde and undergo a practical, useful tandem allylic isomerization-Aldol reaction to afford more functionalized compounds.