Novel Transformation of Methoxy Tetralones During Demethylation with Boron Trifluoride Etherate and Acetic Anhydride

2004 ◽  
Vol 34 (18) ◽  
pp. 3399-3408 ◽  
Author(s):  
Ajoy K. Banerjee ◽  
Liadis Bedoya ◽  
William J. Vera ◽  
Carlos Melean ◽  
Henry Mora ◽  
...  
Keyword(s):  
Acetic Anhydride ◽  
Boron Trifluoride ◽  
Boron Trifluoride Etherate

Novel Transformation of Methoxy Tetralones During Demethylation with Boron Trifluoride Etherate and Acetic Anhydride.

ChemInform ◽  
2005 ◽  
Vol 36 (6) ◽  
Author(s):  
Ajoy K. Banerjee ◽  
Liadis Bedoya ◽  
William J. Vera ◽  
Carlos Melean ◽  
Henry Mora ◽  
...  
Keyword(s):  
Acetic Anhydride ◽  
Boron Trifluoride ◽  
Boron Trifluoride Etherate

Tetracyclic triterpenes. VIII. The skeletal rearrangement of 3β-acetoxy-9α,11α-epoxy-5α-lanostan-7-one: 13- and 10-methyl group migration

1985 ◽  
Vol 63 (6) ◽  
pp. 1280-1286 ◽  
Author(s):  
Zdzisław Paryzek ◽  
Roman Wydra
Keyword(s):  
Acetic Anhydride ◽  
Spectral Data ◽  
Boron Trifluoride ◽  
Boron Trifluoride Etherate ◽  
Major Product ◽  
Chemical Transformations ◽  
Skeletal Rearrangement ◽  
Methyl Group ◽  
Group Migration

The boron trifluoride etherate catalyzed rearrangement of 3β-acetoxy-9α, 11α-epoxy-5α-lanostan-7-one (1) in acetic anhydride resulted in formation of 19(10 → 9β)abeo compounds 2 and 4 along with 18(13 → 12β)abeo compound 5, as the major product. These structures are supported by spectral data and chemical transformations. The possible mechanism of the rearrangement is discussed.

Cyclization of 17-ethylenedioxy-3α,5-cyclo-6,7-seco-5α-androstane-6,7-diol

1979 ◽  
Vol 44 (1) ◽  
pp. 128-144 ◽  
Author(s):  
Helena Velgová ◽  
Dietrich Zeigan ◽  
Günther Engelhardt ◽  
Antonín Trka
Keyword(s):  
Acetic Anhydride ◽  
Intramolecular Cyclization ◽  
Boron Trifluoride ◽  
Boron Trifluoride Etherate ◽  
Mass Spectrometric ◽  
Cyclic Ethers ◽  
Mass Spectrometric Data ◽  
Spectrometric Data ◽  
H Nmr ◽  
C Nmr

Intramolecular cyclization of 17-ethylenedioxy-3α,5-cyclo-6,7-seco-5α-androstane-6,7-diol (I) on treatment with p-toluenesulphonyl chloride in pyridine gives 17-ethylenedioxy-3α,5-cyclo-B-homo-7-oxa-5α-androstane (III) and 17-ethylenedioxy-3,5-methylene-6-oxaandrostane (II). The cyclic ethers II and III after deketalization and treatment with boron trifluoride etherate in acetic anhydride yield 3β,7-dihydroxy-6,7-secoandrost-5-en-17-one (XIV) along with a small quantity of 3β,5-cyclo-A-homo-6-oxa-5β-androstane-17-one (XIII). Proof of the structures in question is based on IR, 1H NMR, 13C NMR and mass spectrometric data.

Synthesis of o-isopentenylphenols

1971 ◽  
Vol 24 (11) ◽  
pp. 2355 ◽  
Author(s):  
J Hlubucek ◽  
E Ritchie ◽  
WC Taylor
Keyword(s):  
Phosphoric Acid ◽  
Zinc Chloride ◽  
Boron Trifluoride ◽  
Boron Trifluoride Etherate ◽  
Stannic Chloride ◽  
Counter Ion

The effect of the solvent and the counter-ion on the ring alkylation of 3- and 4-methoxyphenols by isopentenyl bromide has been examined. Under strictly anhydrous conditions good and consistent yields of the o- isopentenylphenols were obtained with the combination potassium- toluene, but sodium-toluene was more convenient. ��� Boron trifluoride etherate was more satisfactory than stannic chloride, zinc chloride, or phosphoric acid in catalysing the condensation of 3- and 4-methoxy-phenols with 2-methylbut-3-en-2-ol to the corresponding o-isopentenylphenols. Aryl α,α-dimethylpropargyl ethers were partially hydrogenated to the corresponding α,α- dimethylallyl ethers which rearranged in boiling N,N-diethyl-aniline to o-isopentenylphenols in high overall yield.

scholarly journals Synthesis of 5,6,7,8-Tetrahydroquinolines by Thermolysis of Oxime O-Allyl Ethers in the Presence of Boron Trifluoride Etherate.

1993 ◽  
Vol 41 (7) ◽  
pp. 1297-1298 ◽  
Author(s):  
Junko KOYAMA ◽  
Tamaki OGURA ◽  
Kiyoshi TAGAHARA ◽  
Masaaki MIYASHITA ◽  
Hiroshi IRIE
Keyword(s):  
Boron Trifluoride ◽  
Boron Trifluoride Etherate ◽  
Allyl Ethers
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