Derivatives of furyl(diethoxyphosphoryl)acetic aldehyde in Wittig reaction

2017 ◽  
Vol 87 (7) ◽  
pp. 1516-1526 ◽  
Author(s):  
L. M. Pevzner
Keyword(s):  
Wittig Reaction ◽  
Acetic Aldehyde ◽  
Derivatives Of

Preparation of some deuterium labelled 9- and/or 10-oxygenated derivatives of geraniol, geranial, nerol, and neral

1983 ◽  
Vol 61 (6) ◽  
pp. 1053-1059 ◽  
Author(s):  
J. Balsevich
Keyword(s):  
Selective Oxidation ◽  
Wittig Reaction ◽  
Dimethyl Acetal ◽  
Acidic Hydrolysis ◽  
Triphenyl Phosphonium ◽  
Isomeric Purity ◽  
Derivatives Of

The preparation of various deuterium labelled 9- and/or 10-oxygenated derivatives of geraniol, geranial, nerol, and neral is described. Wittig reaction of the tetrahydropyranyl ethers of (E)- and (Z)-1,1-dideutero-6-(triphenylphosphonium)-3-methyl-2-hexen-1-ol iodides (23 and 24) with the tetrahydropyranyl ethers of hydroxyacetone and 1,3-dihydroxyacetone afforded, after deprotection, C-1 dideuterated 9-hydroxygeraniol, 9-hydroxynerol, 9,10-dihydroxygeraniol, and 9,10-dihydroxynerol of high isomeric purity. Selective oxidation of these products allowed for the preparation of the corresponding derivatives possessing an aldehyde functionality at C-9 or C-1 and C-9. Wittig reaction of 23 and 24 with pyruvaldèhyde dimethyl acetal followed by acidic hydrolysis afforded C-1 dideuterated 10-oxogeraniol and 10-oxonerol, oxidation of which yielded C-1 deuterated 10-oxogeranial and 10-oxoneral. Wittig reaction of (E)- and (Z)-1,1-dideutero-6-(triphenyl-phosphonium)-3-methyl-2-hexen-1-ol iodides (49 and 50) with 1,1,3,3-tetraethoxyacetone afforded C-1 dideuterated 9,9,10,10-tetraethoxygeraniol and 9,9.10,10-tetraethoxynerol, oxidation of which provided C-1 deuterated 9,9,10,10-tctraethoxygeranial and 9,9,10,10-tetraethoxyneral.

Synthesis and reactions of β-substituted derivatives of furan

1985 ◽  
Vol 50 (9) ◽  
pp. 2077-2083 ◽  
Author(s):  
Adolf Jurášek ◽  
Vladimír Žvak ◽  
Jaroslav Kováč ◽  
Oľga Rajniaková ◽  
Jarmila Štetinová
Keyword(s):  
Wittig Reaction ◽  
Cycloaddition Reaction ◽  
Uv Spectra ◽  
H Nmr ◽  
Spectral Evidence ◽  
Derivatives Of

The 1,4-cycloaddition reaction of 4-phenyl-1,3-oxazole to 2-propinyl benzoate and dimethyl butinedioate afforded the respective 3-furylmethyl benzoate (I) and 3,4-bis(methoxycarbonyl)furan (II). These compounds served for the synthesis of 3-chloromethylfuran and 3,4-bis(chloromethyl)furan, which afforded via Wittig reaction 3-(β-arylvinyl)furans III (aryl = 5-nitro-2-furyl (IIIa), 5-nitro-2-thienyl (IIIb), 1-methyl-4-nitro-2-pyrrolyl (IIIc), and 4-nitrophenyl (IIIe)) and 3,4-bis(β-arylvinyl)furans IV (aryl = 5-nitrofuryl (IVa), 5-nitro-2-thienyl (IVc), and 4-nitrophenyl (IVd)). According to spectral evidence (1H NMR, IR, UV spectra), compound IIIa and IIIb originated as E isomers, whilst the remaining products are a mixture of E and Z isomers; some couples were succeded to separate.

Wittig type reactions of 2-formylated derivatives of 6-methylergoline - I

1982 ◽  
Vol 47 (6) ◽  
pp. 1636-1640 ◽  
Author(s):  
Jan Beneš ◽  
Jiří Holubek
Keyword(s):  
Wittig Reaction ◽  
Sodium Hydride ◽  
Ethyl Esters ◽  
Acrylic Acids ◽  
Derivatives Of

Using the Horner-Wittig reaction, aldehydes I and II were converted, with high E-selectivity, into ethyl esters of substituted acrylic acids, VI and VII. The N-anions generated by deprotonation of derivative I-V with sodium hydride in tetrahydrofuran reacted with vinyltriphenylphosphonium bromide with the formation of derivatives of pyrrolo[1,2-a]ergoline-I, XI-XV.

Synthesis and Identification of ω-Phenylalkylcatechols in Burmese Lac

1988 ◽  
Vol 41 (1) ◽  
pp. 19 ◽  
Author(s):  
A Jefferson ◽  
MV Sargent ◽  
S Wangchareontrakul
Keyword(s):  
Natural Products ◽  
Catalytic Hydrogenation ◽  
Wittig Reaction ◽  
Spectral Characteristics ◽  
Chromatographic Retention ◽  
Phosphonium Bromide ◽  
Mass Spectral ◽  
Trimethylsilyl Derivatives ◽  
Derivatives Of

The presence of 3-(10′-phenyldecyl)-(2) (2%), 3-(12′-phenyldodecyl)- (3) (6%), 4-(10′-phenyldecyl)-(4) (0.3%) and 4-(12′-phenyldodecyl)- benzene-1,2-diol (5) (0.3%) in Burmese lac , the sap of Melanorrhoea usitata Wall has been confirmed by the synthesis of these compounds and a comparison of the gas chromatographic retention times and the mass spectral characteristics of their bis-O-( trimethylsilyl ) derivatives with the derivatives of the natural products. Typically, 3,4- bis ( benzyloxy ) benzaldehyde (7) on Wittig reaction with triphenyl (11- phenylundecyl ) phosphonium bromide (20) and subsequent catalytic hydrogenation of the resultant olefin gave compound (5) in 59% overall yield.

scholarly journals An expedient synthesis of 5-n-alkylresorcinols and novel 5-n-alkylresorcinol haptens

2009 ◽  
Vol 5 ◽  
Author(s):  
Kirsti Parikka ◽  
Kristiina Wähälä
Keyword(s):  
Wittig Reaction ◽  
Alkyl Chain ◽  
Open Systems ◽  
Aqueous Media ◽  
Whole Grain ◽  
Detection Techniques ◽  
Immunochemical Detection ◽  
Grain Products ◽  
Derivatives Of ◽  
Long Alkyl Chain

The first synthesis of bioactive long alkyl chain 5-n-alkylresorcinols, present in whole grain products, by a novel modification of the Wittig reaction is described. All the main long chain 5-n-alkylresorcinols present in rye and wheat, including C23 and C25 analogues and haptens, which have not been previously prepared, were synthesised. Microwave-promoted reactions of a semi-stabilized ylid and alkanals in water gave good yields in both pressurized and open systems. An alternative microwave-promoted synthesis starting from non-stabilized alkyltriphenylphosphonium salts and 3,5-dimethoxybenzaldehyde worked as well. Aqueous media were suitable for the reactions even if the starting materials were not soluble in water. The 5-n-alkylresorcinols are potential biomarkers of whole grain intake, and the new hapten derivatives of 5-n-alkylresorcinols will open the way for the immunochemical detection techniques of alkylresorcinols.

2001 E.W.R. Steacie Award LectureThe imido ligand in main group element chemistry

2001 ◽  
Vol 79 (12) ◽  
pp. 1841-1850 ◽  
Author(s):  
Tristram Chivers
Keyword(s):  
Wittig Reaction ◽  
Earth Metal ◽  
High Reactivity ◽  
Main Group ◽  
Main Group Chemistry ◽  
Bridging Ligand ◽  
Multiply Bonded ◽  
Oxo Anions ◽  
Metal Derivatives ◽  
Derivatives Of

The imido group (NR) is a versatile ligand in main group chemistry. The high reactivity of multiply bonded (terminal) imido derivatives of p-block elements is used, for example, in the aza-Wittig reaction, allylic aminations, and in peptide synthesis. As a bridging ligand, the imido group provides a cornerstone for a wide variety of binary cluster structures. This review is primarily concerned with the synthesis, structures, reactions, and ligand behaviour of imido derivatives of the heavy chalcogens (selenium and tellurium) as exemplified by the tellurium diimide dimer t-BuNTe(µ-N-t-Bu)2TeN-t-Bu and the homoleptic trisimido-tellurite dianion [Te(N-t-Bu)3]2–. The synthesis and cluster structures of alkali metal and alkaline earth metal derivatives of heteroleptic imido-oxo anions of sulfur, e.g., [OxS(NR)3 – x]2– (x = 1, 2) and [O2S(µ-NPh)SO2]2–, are also discussed.Key words: main group chemistry, imido ligand, chalcogens.

Synthetic Analogues of Prostaglandins F2α and E2

1994 ◽  
Vol 59 (1) ◽  
pp. 138-148 ◽  
Author(s):  
Václav Kozmík ◽  
Jaroslav Paleček
Keyword(s):  
Wittig Reaction ◽  
Hydroxyl Groups ◽  
Phosphonium Salts ◽  
Subsequent Reduction ◽  
Synthetic Analogues ◽  
Derivatives Of

The synthesis of new derivatives of prostaglandins F2α and E2 XIIa,b - XVa,b and XXa,b - XXIIIa,b containing the furan or thiophene nucleus in the upper chain has been accomplished starting from [3aα,4α,5β,6aα]-(±)-hexahydro-5-hydroxy-4-((E)-(3α)-hydroxy-1-octenyl)-2H-cyclopenta[b]furan-2-one (Ia) and [3aα,4α,5β,6aα]-(±)-hexahydro-5-hydroxy-4-[4-(3-chlorophenoxy)-(3α)-hydroxy-1-butenyl]cyclopenta[b]furan-2-one (Ib). The diols Ia and Ib have been converted into the above-mentioned analogues of prostaglandins F2α and E2 by protecting the hydroxyl groups, subsequent reduction and Wittig reaction with the ylides prepared from the phosphonium salts IV - VII, and final deprotection (or oxidation plus deprotection).

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