AN IMPROVED PREPARATION OF ω-HYDROXY ALIPHATIC ACIDS AND THEIR ESTERS

1960 ◽  
Vol 38 (10) ◽  
pp. 1976-1982 ◽  
Author(s):  
D. G. M. Diaper ◽  
D. L. Mitchell
Keyword(s):  
Sodium Borohydride ◽  
Reductive Cleavage ◽  
Aliphatic Acids ◽  
Aliphatic Esters ◽  
High Yields

Reductive cleavage of the ozonides of aliphatic acids and their esters by sodium borohydride or by hydrogenation produces ω-hydroxy aliphatic acids and ω-hydroxy aliphatic esters, respectively, in high yields.

Reductions with sulfurated borohydrides. V. Reductions of ketones

1970 ◽  
Vol 48 (15) ◽  
pp. 2366-2371 ◽  
Author(s):  
J. M. Lalancette ◽  
A. Freche
Keyword(s):  
High Temperature ◽  
Carbonyl Group ◽  
Sodium Borohydride ◽  
Room Temperature ◽  
High Yield ◽  
High Yields ◽  
Very High

Ketones can be reduced with sulfurated sodium borohydride. Very high yield (≈90%) of the corresponding alcohol is obtained with the appropriate ratio of ketone and hydride at room temperature. The reaction is much influenced by the steric environment around the carbonyl group. At high temperature (65°) disulfides and tetrasulfides are produced. In some cases the structure of those sulfides have been established. Conjugated ketones can be reduced to the corresponding alcohols with very high yields.

Cyano esters and malononitriles. IV. Cyano(fluorenyl)acetohydrazides and fluorenylpyrazolones

1977 ◽  
Vol 30 (10) ◽  
pp. 2255 ◽  
Author(s):  
N Latif ◽  
N Mishriky ◽  
M Hammad
Keyword(s):  
Phthalic Anhydride ◽  
Sodium Borohydride ◽  
Succinic Anhydride ◽  
Reductive Cleavage ◽  
Open Chain ◽  
Chain Compounds

Cyano(fluoren-9-yl)acetohydrazides cyclize readily under acid or basic conditions to give 3-amino-4-(9-substituted fluoren-9-yl)pyrazol-5(4H)- ones (3). Upon thermolysis of the hydrazides the pyrazolones and/or dimeric products are produced.��� The cyanoacetohydrazides condense with phthalic anhydride to give the 2-(fluoren-9-yl)-N-phthalimidoacetamides(7), whereas, with succinic anhydride, the open-chain compounds (10) are obtained which upon thermolysis afford the dimeric compounds (6). The acetamides (7) undergo unusual reductive cleavage with sodium borohydride affording the fluorenylpyrazolones (3). Electronic, infrared and N.M.R. spectra of the products are discussed.

Facile Synthesis of Thiols and Sulfides

1975 ◽  
Vol 53 (10) ◽  
pp. 1480-1483 ◽  
Author(s):  
Jean-Rock Brindle ◽  
Jean-Louis Liard
Keyword(s):  
Aromatic Ring ◽  
Sodium Borohydride ◽  
Facile Synthesis ◽  
Experimental Conditions ◽  
The Stability ◽  
High Yields

Sulfurated sodium borohydride reacts with benzylic halides to give high yields of α-toluenethiol or benzylic polysulfldes depending upon the experimental conditions and the mode of hydrolysis.Aliphatic halides and dibenzylic halides react in the same manner as benzylic halides for a given experimental condition whereas benzylic halides substituted with other groups can be totally or partially reduced depending on the stability of the substituent towards NaBH2S3.Halogens directly attached on the aromatic ring do not react with NaBH2S3.

Chemistry of the Podocarpaceae. XLVIII. Photo-sensitized oxidations of unsaturated ring-c aromatic diterpenoids

1974 ◽  
Vol 27 (9) ◽  
pp. 2001 ◽  
Author(s):  
RC Cambie ◽  
RC Hayward
Keyword(s):  
Sodium Borohydride ◽  
Convenient Method ◽  
Lithium Aluminium ◽  
Enol Acetates ◽  
High Yields ◽  
General Method

Photo-sensitized oxidation of the 6,7-dehydro ring-c aromatic diterpenoids (5), (8) and (38) affords high yields of the corresponding 5-ene-7-ones (62), (63) and (69). Similar oxygenation of 13-methoxy- totara-6,8,11,13-triene (21) gives a hydroperoxide (74) which undergoes a facile rearrangement to a naphthyl derivative (80) in the presence of acid. Photo-sensitized oxidation of the enol acetates derived from the 7-oxo diterpenoids, however, provides a general method for preparation of the corresponding 5-ene-7-one. Reduction of the enone (62) with lithium aluminium hydridealuminium chloride gives a mixture of the 5,8,11,13-tetraene (66) and the 6,8,11,13-tetraene (9) while reduction with sodium borohydride and treatment of the resulting alcohols (61) and (67) with acid gives a mixture of the tetraenes (5) and (68). Photo-oxygenation of the latter mixture provides a convenient method for isolating the tetraene (68). Similar reductions of 13-methoxytotara-5,8,11,13-tetraen-7-one (76) have been examined and products from the action of m-chloroperbenzoic acid on the enol acetates (19), (20) and (7) are reported.

Nucleic acid related compounds. 67. Synthesis of 5′-amino and 5′-methylthio chain-extended nucleosides from uridine

1991 ◽  
Vol 69 (12) ◽  
pp. 2104-2111 ◽  
Author(s):  
Stanislaw F. Wnuk ◽  
N. Kent Dalley ◽  
Morris J. Robins
Keyword(s):  
Nucleic Acid ◽  
Sodium Borohydride ◽  
Conjugate Addition ◽  
Amino Derivative ◽  
Vinyl Sulfone ◽  
X Ray ◽  
Basic Solutions ◽  
High Yields ◽  
Wittig Reagent ◽  
Related Compounds

Treatment of 2′,3′-O-isopropylideneuridine-5′-aldehyde with the stabilized Wittig reagent, (p-toluenesulfonylmethylene)triphenylphosphorane, gave high yields of 1-[5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-ribo-hex-5(E)-enofuranosyl]uracil (2). This vinylsulfone (2) underwent isomerization readily in base to give the allylic sulfone, 1-[5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-erythro-hex-4(Z)-enofuranosyl]uracil (3). Treatment of 2 or 3 with aqueous trifluoroacetic acid gave the corresponding deprotected vinyl (5) or allylic (6) sulfones, and 5 was converted to 6 readily in basic solutions. Treatment of 2 with sodium borohydride, sodium thiomethoxide, or ammonia resulted in conjugate addition (at C5′ of the vinyl sulfone) to give the 5′-hydro, 5′-methylthio, or 5′-amino-5′,6′-dideoxy-6′-(p-toluenesulfonyl) nucleosides. The 5′-substituted diastereomers were deprotected, separated, and the configuration of a 5′-amino derivative was established by X-ray crystallography.Key words: allylic sulfones, amino-nucleosides, 5′,6′-dideoxynucleosides, nucleosides, uridine, vinyl sulfones.

scholarly journals Amino acids and peptides. XXVII. A novel reductive cleavage of N-C-N bonds with sodium borohydride.

1977 ◽  
Vol 25 (7) ◽  
pp. 1559-1565 ◽  
Author(s):  
KAZUO MURATO ◽  
TAKAYUKI SHIOIRI ◽  
SHUNICHI YAMADA
Keyword(s):  
Amino Acids ◽  
Sodium Borohydride ◽  
Reductive Cleavage
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