Alkyl nitrite-metal halide deamination reactions. 6. Direct synthesis of arenediazonium tetrafluoroborate salts from aromatic amines, tert-butyl nitrite, and boron trifluoride etherate in anhydrous media

1979 ◽  
Vol 44 (9) ◽  
pp. 1572-1574 ◽  
Author(s):  
Michael P. Doyle ◽  
William J. Bryker
Keyword(s):  
Aromatic Amines ◽  
Boron Trifluoride ◽  
Direct Synthesis ◽  
Boron Trifluoride Etherate ◽  
Metal Halide ◽  
Tert Butyl ◽  
Alkyl Nitrite

Synthesis of optically active l-acyl-2-O-alkyl-sn-glycero-3-phosphocholine via 1-O-benzyl-sn-glycerol 3-arenesulfonate

1990 ◽  
Vol 68 (1) ◽  
pp. 360-365 ◽  
Author(s):  
Shaukat Ali ◽  
Robert Bittman
Keyword(s):  
Benzyl Alcohol ◽  
Alkyl Group ◽  
Boron Trifluoride ◽  
Enantiomeric Excess ◽  
Boron Trifluoride Etherate ◽  
Optically Active ◽  
Epoxide Ring ◽  
Phospholipid Synthesis ◽  
Tert Butyl ◽  
Very High

A stereocontrolled route to 1-palmitoyl-2-O-hexadecyl-sn-glycero-3-phosphocholine from (R)-glycidyl tosylate is described. This method gives very high enantioselectivity (93–96% enantiomeric excess) and can be used to prepare 3-acyl-2-O-alkyl-sn-glycero-1-phosphocholines from (S)-glycidyl tosylate. The key step is the preparation of 1-O-benzyl-sn-glycerol 3-tosylate by the boron trifluoride etherate catalyzed regio- and stereo-specific opening of the epoxide ring with excess benzyl alcohol. The alkyl group is introduced using alkyl trifluoromethanesulfonate in the presence of excess 2,6-di-tert-butyl-4-methylpyridine. Debenzylation gives 2-O-alkyl-sn-glycerol 3-arenesulfonate, which is acylated and then converted into the phosphocholine. The use of chiral glycidyl derivatives as starting materials for the synthesis of glycerophospholipids is discussed.Key words: acylalkylglycerophospholipids, phospholipid synthesis, glycidyl derivatives in phospholipid synthesis, epoxides as precursors of phospholipids.

Preparation of 7-spiroepoxy and 7,7-disubstituted cephalosporanate 1,1-dioxide from 7-diazocephalosporanate 1,1-dioxide: Reactions of 7-diazocephalosporanate 1,1-dioxide with aldehydes

1991 ◽  
Vol 56 (11) ◽  
pp. 2352-2361 ◽  
Author(s):  
David Czajkowski ◽  
Oludotun A. Phillips ◽  
Narender A. V. Reddy ◽  
Paul Spevak ◽  
Bruce Lix ◽  
...  
Keyword(s):  
Boron Trifluoride ◽  
Boron Trifluoride Etherate ◽  
Tert Butyl ◽  
Profound Influence ◽  
Carbonyl Products

The reactions of tert-butyl-3-acetoxymethyl-3-cephem-7-diazocephalosporanate 1,1-dioxide (I) with acetaldehyde, benzaldehyde, 2-thiophene caboxaldehyde, 3-thiophene carboxaldehyde, 2-furan carboxaldehyde, 3-furan carboxaldehyde and isobutyraldehyde have been studied. Use of boron trifluoride etherate as a catalyst for these reactions was found to accelerate the reactions markedly and to favour the formation of aldehydes rather than the ketones at C-7 position as the carbonyl product. The products obtained from these reactions and the ratios of carbonyl products to epoxides suggest that the R groups of the carbonyl component have profound influence on the reactions.

Catalyst- and solvent-free Csp2-H functionalization of 4-hydroxycoumarins via C-3 dehydrogenative aza-coupling under ball-milling

2021 ◽  
Author(s):  
Goutam Brahmachari ◽  
Indrajit Karmakar ◽  
Pintu Karmakar
Keyword(s):  
Ball Milling ◽  
Aromatic Amines ◽  
Solvent Free ◽  
One Pot ◽  
Biologically Relevant ◽  
Tert Butyl ◽  
Three Component Reaction ◽  
Primary Aromatic Amines

A one-pot procedure for the synthesis of biologically relevant coumarin-hydrazones by a three-component reaction between 4-hydrocoumarins, primary aromatic amines and tert-butyl nitrite under ball-milling in the absence of any catalyst/additive...

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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