Reaction of amines with the bisulphite addition compound of 5-Amino-5-deoxy-D-xylose: Conversion to piperidine derivatives

1966 ◽  
Vol 19 (4) ◽  
pp. 675 ◽  
Author(s):  
DL Ingles
Keyword(s):  
Formic Acid ◽  
Sulphur Dioxide ◽  
Sodium Periodate ◽  
Membered Ring ◽  
Compound Viii ◽  
Barium Salt ◽  
Addition Compound ◽  
Piperidine Derivative ◽  
Enzymic Browning ◽  
Pyridine Salt

The bisulphite addition compound (1) of 5-amino-5-deoxy-D-xylose reacted with cyclohexylamine to form the acyclic derivative (11). With ammonia, benzylamine, morpholine, and piperidine, corresponding salts (IV) of the piperidine derivative D-ido(gluco)-3,4,5-trihydroxy-2-sulphopiperidine (VIII), were isolated. Removal of the amine yielded the crystalline bisulphite addition compound (VIII). Acetylation in the presence of pyridine of the different amine salts (11, IV) and of (VIII) gave an identical acetate (VII), l-acetyl-D-ido(gluco)-3,4,5-triacetoxy-2-sulphopiperidine, isolated as the pyridine salt. Deacetylation of (VII) with barium methoxide gave the barium salt (IX). Oxidation of (IX) with sodium periodate liberated one mole of formic acid, confirming the presence of a six-membered ring containing nitrogen. The significance of these results in the inhibition of non-enzymic browning by sulphur dioxide is discussed.

Energies of interaction and other properties of clathrate compounds

1954 ◽  
Vol 223 (1153) ◽  
pp. 238-250 ◽  
Keyword(s):  
Formic Acid ◽  
Hydrogen Chloride ◽  
Sulphur Dioxide ◽  
Hydrogen Bromide ◽  
Energy Difference ◽  
Heats Of Formation ◽  
Free Energies ◽  
Clathrate Compounds ◽  
Intermolecular Contacts

Heats of formation of clathrate compounds of β-quinol with argon, oxygen, nitrogen, hydrogen chloride, hydrogen bromide, formic acid and methanol have been determined calorimetrically. For the argon and oxygen compounds, the heats of formation were determined for samples of widely differing composition, and they vary linearly with the fraction of available spaces filled. Using the energy difference between α- and β-quinol obtained directly or by extrapolation of the measurements on the argon and oxygen compounds, the energies of interaction of the enclosed molecules with the β-quinol cage have been determined. Their values are interpreted in terms of the polarizabilities of the enclosed molecules and the number of intermolecular contacts occurring. The free energies of formation, and the colours of the sulphur dioxide and oxygen clathrate compounds are also discussed briefly.

scholarly journals The Conformation of a Nine-membered Ring. Crystal Structure of the 1:1 Addition Compound Mercuric Chloride-Cyclononanone.

1971 ◽  
Vol 25 ◽  
pp. 1114-1124 ◽  
Author(s):  
S. Dahl ◽  
P. Groth ◽  
Manohar Singh Sood ◽  
Bent Eichstedt Nielsen ◽  
Hans Ljunggren ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Mercuric Chloride ◽  
Membered Ring ◽  
Addition Compound

The Chemistry of Laurenene. XII. The Structure of a Minor Product From the Formic Acid Induced Rearrangement of Lauren-1-ene

1990 ◽  
Vol 43 (6) ◽  
pp. 1061 ◽  
Author(s):  
AR Hayman ◽  
NB Perry ◽  
RT Weavers
Keyword(s):  
Formic Acid ◽  
Membered Ring ◽  
Carbon Skeleton ◽  
A Minor

Rearrangement of lauren-1-ene (1) with formic acid gives a trisubstituted alkene (4) in addition to the previously characterized tetrasubstituted alkene (3). The structure was determined by n.m.r . Studies on (4) and the derived diol (5). Alkene (4) contains a new tetracyclic carbon skeleton which comprises one six- membered ring and three five- membered rings.

Chemistry of non-enzymic browning. V. The preparation of Aldose-Potassium bisulphite addition compounds and some amine derivatives

1959 ◽  
Vol 12 (1) ◽  
pp. 97
Author(s):  
DL Ingles
Keyword(s):  
Addition Compound ◽  
Sodium Bisulphite ◽  
Enzymic Browning ◽  
New Compounds

From the reaction of potassium bisulphite with D-glucose the glucose-potassium bisulphite addition compound, D-glycero-D-ido-1,2,3,4,5,6-hexahydroxyhexyl potassium sulphonate was prepared pure and crystalline. Similar new compounds were prepared from the reaction of potassium bisulphite with D-galactose, L-rhamnose, D-mannose, and L-arabinose. The reaction of the glucose-potassium bisulphite addition compound with aniline, gave pure crystalline D-glycero-D-ido-1-anilino-2,3,4,5,6-pentahydroxyhexyl potassium sulphonate. Similar derivatives were prepared from p-toluidine, p-anisidine, and o-phenylenediamine. The aniline and p-toluidine derivatives were also prepared from the glucose-sodium bisulphite addition compound.

Synthesis and conformations of α-aminoadipyl- and glycyl-α-aminoadipylthiazepine sulfoxides

1981 ◽  
Vol 59 (2) ◽  
pp. 406-421 ◽  
Author(s):  
Saul Wolfe ◽  
Raymond John Bowers ◽  
Syed Khaqan Hasan ◽  
Peter Michael Kazmaier
Keyword(s):  
Hydrogen Bond ◽  
Carbon Atom ◽  
Formic Acid ◽  
Chair Conformation ◽  
Membered Ring ◽  
Amide Proton ◽  
Penicillin Biosynthesis ◽  
Boat Conformation ◽  
Internal Hydrogen Bond ◽  
Twist Boat

The title compounds, having the R-absolute configurations at sulfur, and labelled with 14C at carbons 5, 6, and 7 of the seven-membered ring, have been synthesized by condensation of isotopically labelled 3D-benzhydryloxycarbonyl-6L-amino-2,2-dimethyl-5-oxoperhydro-1,4-thiazepine with N-Boc- and α-benzhydryl-protected L-α-aminoadipic acid and glycyl-L-α-aminoadipic acid, followed by oxidation with m-chloroperoxybenzoic acid and complete deprotection with formic acid. The conformations of the sulfoxides, and related thiazepines and thiazepine sulfoxides, have been examined by 1Hmr spectroscopy. All thiazepines, and the two title sulfoxides, appear to exist in a twist boat conformation. Most other sulfoxides exist in a chair conformation, which is stabilized by an internal hydrogen bond between the sulfinyl oxygen and the amide proton at C6; when this hydrogen bond is not present, both chair and twist boat conformations may be observable. The title compounds are of interest as possible intermediates in penicillin biosynthesis from glycyl-δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine (GACV) or ACV, according to a new theory, which deals, in particular, with the stereochemical course of the biosynthesis at the beta (β) carbon atom of valine.

Corrosion of bronze by acetic and formic acid vapours, sulphur dioxide and sodium chloride particles

1995 ◽  
Vol 46 (9) ◽  
pp. 515-519 ◽  
Author(s):  
J. M. Bastidas ◽  
B. Chico ◽  
M. P. Alonso ◽  
E. M. Mora
Keyword(s):  
Sodium Chloride ◽  
Formic Acid ◽  
Sulphur Dioxide

Zur Chemie des Phorbols, VII

1968 ◽  
Vol 23 (12) ◽  
pp. 1579-1583 ◽  
Author(s):  
Michael Gschwendt ◽  
Eckhart Härle ◽  
Erich Hecker
Keyword(s):  
Acetic Acid ◽  
Sodium Periodate ◽  
Membered Ring

Cleavage of phorbol-3-ol-12,13,20-triacetate with sodium-periodate proves the presence of an α,β- unsaturated tertiary 1,2-ketol group in phorbol and its location in the five-membered ring. Accordingly 4-O-methyl-phorbol-3-ol-12,13,20-triacetate is not cleaved by sodium periodate, and by zinc/acetic acid phorbol-12,13,20-triacetate is converted to a 4-deoxy-compound.

Diterpene Imines. The Preparation of 2-Azalauren-1-ene and the Facile Autoxidation of 6-Azadihydrorimuene

1990 ◽  
Vol 43 (4) ◽  
pp. 719 ◽  
Author(s):  
AR Hayman ◽  
LR Hanton ◽  
RT Weavers
Keyword(s):  
Formic Acid ◽  
Membered Ring ◽  
Keto Acid ◽  
X Ray ◽  
Model Studies ◽  
Crystallographic Study

2-Azalauren-1-ene (2) has been synthesized from keto acid (5), but attempts to generate its C15 epimer (19) have produced only (2). Model studies of imine production by treatment of a rimuene -derived keto acid (3) with iodosylbenzene /formic acid have produced a hydroxy imine (11), a conjugated imine (13), and a keto lactam (12) which has a ten-membered ring. An X-ray crystallographic study which proves the structure of (12) is described. Data in support of the intermediacy of imine (7) (6-azadihydrorimuene) in the production of (11), (12) and (13) have been obtained.

Chemistry of Non-Enzymic Browning. XI. The Reactions of Bisulphite with Reducing Sugars

1960 ◽  
Vol 13 (3) ◽  
pp. 404 ◽  
Author(s):  
DL Ingles
Keyword(s):  
Ascorbic Acid ◽  
Sulphur Dioxide ◽  
Reducing Sugars ◽  
Complex Mixture ◽  
Dehydroascorbic Acid ◽  
Keto Acids ◽  
Enzymic Browning

The reactions of reducing sugars with bisulphite have been studied at 100 �C and lower temperatures. Reducing sugars promoted the autoxidation of bisulphite to sulphur and sulphate, the ketoses being more effective than the aldoses. During the autoxidation the aldoses were oxidized, in part, to the corresponding aldonic acids. The ketose sugars reacted more rapidly and extensively than the aldoses, only 32 per cent. of unchanged fructose being recovered after 8 hr at 100 �C. Oxidation of the ketoses probably occurred via the osone and gave a complex mixture of keto acids. Ascorbic acid was converted to dehydroascorbic acid and an unidentified acid. The reactions offer possible explanations for the formation of sulphate and the loss of bisulphite observed during storage of foods treated with sulphur dioxide. An oxidative mechanism has been suggested for the inhibition of non-enzymic browning by sulphur dioxide.

scholarly journals Mechanism of Reduction of Sulphur Dioxide by Formic Acid.

1962 ◽  
Vol 16 ◽  
pp. 570-574
Author(s):  
Marit Goliath ◽  
Bengt O. Lindgren ◽  
Preben C. Mörk ◽  
G. A. Sim ◽  
Olof Theander ◽  
...  
Keyword(s):  
Formic Acid ◽  
Sulphur Dioxide
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