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Carbonyl compounds, reaction with

The reaction of phosphazenes with carbonyl compounds is an excellent tool for the formation of carbon-nitrogen double bonds and this reaction seems to be one of the most efficient methods for the creation of the imine group under mild reaction conditions.  [Pg.440]

Conjugated phosphazenes have been widely used for the preparation of azadienes. An important extension of the aza-Wittig/intramolecular electrocyclic ring closure (AW-IEC) methodology has been used in the construction of j8-carboline alkaloids, which contain a [Pg.440]

3 Reaction of Phosphazenes with Carboxylic Acid Derivatives [Pg.443]

The reaction of acyl halides with phosphazenes gives an mild method for the preparation of 2,5-disustituted oxazoles. This method has been used in the preparation of naturally occurring oxazole alkaloids, such as pimprinine analogues 35a, ° 0-methylhalfordinol (35b) and annuloline (35c). ° The preparation of five pimprinine analogues through [Pg.443]

The same strategy has been reported for the synthesis of the marine alkaloid ahnazole C, isolated from the red seaweed Heraldiophylum sp., which showed antibacterial activity against Gram-negative pathogens. The formation of the central 2,5-disubstituted oxazole [Pg.444]


Although several experimental data concerning the functionalization of cumulenic anions are availab. a (for a review see Ref. 10) (Table I), it remains difficult to predict the compos tion of the product of a particular reaction on a rationalistic basis. Especially the outcome of reactions with carbonyl compounds seems to be... [Pg.28]

Reaction With Carbonyl Compounds. Primary and secondary nitroparaffins undergo aldol-type reactions with a variety of aldehydes and ketones to give nitro alcohols (11). Those derived from the lower nitroparaffins and formaldehyde are available commercially (see Nitro alcohols). Nitro alcohols can be reduced to the corresponding amino alcohols (see Alkanolamines). [Pg.100]

A-Substituted pyrroles, furans and dialkylthiophenes undergo photosensitized [2 + 2] cycloaddition reactions with carbonyl compounds to give oxetanes. This is illustrated by the addition of furan and benzophenone to give the oxetane (138). The photochemical reaction of pyrroles with aliphatic aldehydes and ketones results in the regiospecific formation of 3-(l-hydroxyalkyl)pyrroles (e.g. 139). The intermediate oxetane undergoes rearrangement under the reaction conditions (79JOC2949). [Pg.67]

Pyrazolones show a great variety of reactions with carbonyl compounds (B-76MI40402). For instance, antipyrine is 4-hydroxymethylated by formaldehyde and it also undergoes the Mannich reaction. Tautomerizable 2-pyrazolin-5-ones react with aldehydes to yield compound (324) and with acetone to form 4-isopropylidene derivatives or dimers (Scheme 8 Section 4.02.1.4.10). [Pg.242]

There have been few mechanistic studies of Lewis acid-catalyzed cycloaddition reactions with carbonyl compounds. Danishefsky et ah, for example, concluded that the reaction of benzaldehyde 1 with trans-l-methoxy-3-(trimethylsilyloxy)-l,3-di-methyl-1,3-butadiene (Danishefsky s diene) 2 in the presence of BF3 as the catalyst proceeds via a stepwise mechanism, whereas a concerted reaction occurs when ZnCl2 or lanthanides are used as catalysts (Scheme 4.3) [7]. The evidence of a change in the diastereochemistry of the reaction is that trans-3 is the major cycloaddition product in the Bp3-catalyzed reaction, whereas cis-3 is the major product in, for example, the ZnCl2-catalyzed reaction - the latter resulting from exo addition (Scheme 4.3). [Pg.154]

Allylboron compounds have proven to be an exceedingly useful class of allylmetal reagents for the stereoselective synthesis of homoallylic alcohols via reactions with carbonyl compounds, especially aldehydes1. The reactions of allylboron compounds and aldehydes proceed by way of cyclic transition states with predictable transmission of olefinic stereochemistry to anti (from L-alkene precursors) or syn (from Z-alkene precursors) relationships about the newly formed carbon-carbon bond. This stereochemical feature, classified as simple diastereoselection, is general for Type I allylorganometallicslb. [Pg.260]

In this section alkylation, Michael additions, hydroxyalkylation (reaction with carbonyl compounds), aminoalkylation, acylation and some other reactions of a-sulphinyl carbanions will be discussed. [Pg.305]

Reaction of a-phenylsulfinyl acetate or ethyl a-(t-butylsulfmyl)acetate with one equivalent of ethylmagnesium bromide or iodide was shown to give the corresponding Grignard reagent 129 or 132, which upon reaction with carbonyl compounds afforded the corresponding adducts. Thus Nokami and coworkers prepared ethyl / -hydroxycarboxylates 130167, jS-keto esters 131168, a,/J-unsaturated esters 133169 and other derivatives by this method. [Pg.614]

The decarboxylation reaction usually proceeds from the dissociated form of a carboxyl group. As a result, the primary reaction intermediate is more or less a carbanion-like species. In one case, the carbanion is stabilized by the adjacent carbonyl group to form an enolate intermediate as seen in the case of decarboxylation of malonic acid and tropic acid derivatives. In the other case, the anion is stabilized by the aid of the thiazolium ring of TPP. This is the case of transketolases. The formation of carbanion equivalents is essentially important in the synthetic chemistry no matter what methods one takes, i.e., enzymatic or ordinary chemical. They undergo C—C bond-forming reactions with carbonyl compounds as well as a number of reactions with electrophiles, such as protonation, Michael-type addition, substitution with pyrophosphate and halides and so on. In this context,... [Pg.337]

The availability of the tetrahalogenoanthranilic acids, in particular tetrachloroanthranilic acid, suggested that an investigation of reactions with carbonyl compounds would be worthwhile. The reactions of arynes... [Pg.69]

Other aromatic heterocycles undergo Patemo-Btichi reaction with carbonyl compounds, although these reactions have seldom been applied to organic synthesis. For example, thiophene reacts cleanly with benzaldehyde to afford a single exo product in 63% yield87. Pyrroles also react with aldehydes and ketones however, as a result of the lability of the presumed initial cycloadducts, the only products isolated, even with the rigorous exclusion of acid, are the 3-hydroxyalkylpyrroles 200 (equation 7)89. [Pg.305]

Although a cobalt-catalyzed intermolecular reductive aldol reaction (generation of cobalt enolates by hydrometal-lation of acrylic acid derivatives and subsequent reactions with carbonyl compounds) was first described in 1989, low diastereoselectivity has been problematic.3 6 However, the intramolecular version of this process was found to show high diastereoselectivity (Equation (37)).377,377a 378 A Co(i)-Co(m) catalytic cycle is suggested on the basis of deuterium-labeling studies and the chemistry of Co(ll) complexes (Scheme 81). Cobalt(m) hydride 182, which is... [Pg.447]

In recent years, Hoppe s group has considerably extended the isomerization-addition methodology, especially for the highly regio- and stereoselective synthesis of 1,2-alkadienyl carbamates. It involves deprotonation of alkynyl carbamates, transme-talation into a titanium species and subsequent reaction with carbonyl compounds [26-30]. This group recently described the preparation of enantiomerically enriched 4-hydroxyallenyl carbamates 22 by sparteine-mediated lithiation of alkynyl carbamates 20 [29]. Impressive examples of these transformations are summarized in Scheme 8.8. [Pg.429]

Aldehydes and ketones are formed in reactions with carbonyl compounds, e.g. oximes, diacetyl and CO + tetraalkyltin172 (see also Zollinger7 11). [Pg.657]

Analogous to its reaction with carbonyl compounds (see 6.3.4), benzyltrimethyl-silane undergoes a fluoride-induced nucleophilic substitution reaction on pyridine-1-oxides and quinoline-l-oxide to form 2-benzylpyridines (>70%) and 2-benzyl-quinoline (65%), respectively [57], Allyltrimethylsilane reacts with pyridine-l-oxide to produce 2-propenylpyridine (56%). [Pg.298]

The successful synthesis of 2-thienyl and substituted 2- and 3-thienyl-acetylenes in yields as high as 60-80% opened a wide variety of synthetic applications. Various addition reactions with carbonyl compounds or epoxides could be carried out with ease. Aliphatic as well as aromatic amine addition reactions, or condensation reactions with hydrazine or hydroxylamine could be easily performed. [Pg.143]

For primary alkyl phenyl ethers 47, their hthiation under catalytic conditions (DTBB, 5%) in THF at room temperature gave the expected alkyUithiums, which by reaction with carbonyl compounds afforded, after hydrolysis, the expected alcohols 48 (Scheme 15) . In this case, only the O—Caiiyi bond cleavage was observed . On the other hand, the reaction shown in Scheme 15 failed for secondary (R = i-Pr) or tertiary (R = f-Bu) starting materials. [Pg.658]

Tetrahydrofuran itself can be opened using either the stoichiometric or the catalytic version of arene-promoted lithiation, but both cases need the activation by boron trifluoride. The catalytic reaction was performed by treating the solvent THF 324 with the complex boron trifluoride-etherate and a catalytic amount (4%) of naphthalene. The intermediate 325 was formed. Further reaction with carbonyl compounds and flnal hydrolysis yielded the expected 1,5-diols 326 (Scheme 95), which could be easily cyclized to the corresponding substituted tetrahydropyrans under acidic conditions (concentrated FlCl). [Pg.702]


See other pages where Carbonyl compounds, reaction with is mentioned: [Pg.226]    [Pg.43]    [Pg.86]    [Pg.366]    [Pg.121]    [Pg.49]    [Pg.168]    [Pg.637]    [Pg.828]    [Pg.260]    [Pg.345]    [Pg.38]    [Pg.69]    [Pg.334]    [Pg.64]    [Pg.768]    [Pg.31]    [Pg.655]    [Pg.676]   
See also in sourсe #XX -- [ Pg.860 , Pg.861 ]

See also in sourсe #XX -- [ Pg.860 , Pg.861 ]

See also in sourсe #XX -- [ Pg.860 , Pg.861 ]




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1,3-Pentadiene reactions with carbonyl compounds

1.3- Butadiene reactions with carbonyl compounds

2-Azapentadienyl anion reaction with carbonyl compounds

Acetylides reactions with carbonyl compounds

Alcohols from Reaction of Carbonyl Compounds with Grignard Reagents

Alcohols reaction with carbonyl compound

Alkyl metals, a-selenocarbonyl compound homologation reactions with carbonyl compounds

Alkylation with Carbonyl Compounds The Prins Reaction

Allene, reaction with carbonyl compounds

Allyl acetates reactions with carbonyl compounds

Allyl reaction with carbonyl compounds

Allylation reactions with carbonyl compounds

Allylic acetates reactions with carbonyl compounds

Allylsilanes reactions with carbonyl compounds

Allylstannanes reactions with carbonyl compounds

Allylthiol reactions with carbonyl compounds

Amines reaction with carbonyl compounds

Amino reaction with carbonyl compound

Arsonium ylides reaction with carbonyl compounds

Benzothiazole, 2-alkylmetallated reactions with carbonyl compounds

Biphilic Reactions with Carbonyl Compounds

Borane, dialkylcrotylisomerization reactions with carbonyl compounds

Boranes reaction with halo carbonyl compounds

Borohydride reaction with carbonyl compounds

Carbanions addition reactions with carbonyl compounds

Carbene complexes reactions with carbonyl compounds

Carbene complexes, alkyl pentacarbonylalkylation reaction with carbonyl compounds

Carbonyl complexes, reaction with organomagnesium compound

Carbonyl compounds 1,4-addition reactions with

Carbonyl compounds 1,4-addition reactions with cyanohydrin ethers

Carbonyl compounds 1,4-addition reactions with cyanohydrins

Carbonyl compounds acid derivatives reactions with organometallic reagents

Carbonyl compounds addition reactions with alcohols

Carbonyl compounds photocycloaddition reactions with alkenes

Carbonyl compounds reaction with alanines

Carbonyl compounds reaction with alcohols to form hemiacetal

Carbonyl compounds reaction with benzylic

Carbonyl compounds reaction with bisulfite

Carbonyl compounds reaction with boron reagents

Carbonyl compounds reaction with cyanide

Carbonyl compounds reaction with diazoalkanes

Carbonyl compounds reaction with enol silanes

Carbonyl compounds reaction with nitriles

Carbonyl compounds reaction with organocuprates

Carbonyl compounds reaction with sodium borohydrid

Carbonyl compounds reaction with sodium borohydride

Carbonyl compounds reaction with trialkylboranes

Carbonyl compounds reaction with water

Carbonyl compounds reactions with a-selenoalkylmetals

Carbonyl compounds reactions with allenylsilanes

Carbonyl compounds reactions with allylic sulfinyl carbanions

Carbonyl compounds reactions with crotyl organometallics

Carbonyl compounds reactions with nucleophile

Carbonyl compounds reactions with nucleophiles

Carbonyl compounds reactions with organometallic reagents

Carbonyl compounds reactions with organometallics

Carbonyl compounds reactions with organosamarium ‘ate’ complexes

Carbonyl compounds reactions with selenium-stabilized carbanions

Carbonyl compounds reactions with sulfonimidoyl carbanions

Carbonyl compounds reactions with sulfonyl-stabilized carbanions

Carbonyl compounds, a-seleno reactions with enals

Carbonyl compounds, reaction with ammonia

Carbonyl compounds, reaction with hydrazine

Carbonyl compounds, reaction with methylene equivalents

Carbonyl compounds, reaction with phosphines

Carbonyl compounds, reactions

Carbonyl compounds, reactions with organolithiums or Grignard reagents

Carbonyl compounds, reactions with silenes

Cobalt, octacarbonylbiscatalyst silane reaction with carbonyl compounds

Condensation of Phosphonium Ylides with Carbonyl Compounds Wittig Reaction

Cumulative Subject reaction with carbonyl compounds

Cyanohydrin esters reactions with carbonyl compounds

Cyanohydrin ethers reactions with carbonyl compounds

Cycloaddition Reactions of Carbonyl Compounds with Alkenes

Cyclopropanecarboxylic acid, 2-silyloxyhomoenolate equivalents reactions with carbonyl compounds

Diazo compounds, reactions with metal carbonyls

Diazo reaction with carbonyl compounds

Diols reaction with carbonyl compounds

Enol esters reaction with carbonyl compounds

Enol ethers reaction with carbonyl compounds

Enol sulfonates reaction with carbonyl compounds

Enolates reaction with carbonyl compounds

Ether, benzyl chloromethyl reaction with carbonyl compounds

Furan, 2,5-bis reaction with carbonyl compounds

Furan, 2,5-bis reaction with carbonyl compounds from succinic anhydrides

Furan, 2,5-bis reaction with carbonyl compounds synthesis

Furan, 2,5-bis reaction with carbonyl compounds titanium tetrachloride catalyst

Furan, 2-trimethylsiloxyaldol condensation reaction with carbonyl compounds

Grignard reaction: alkylation with carbonyl compounds

Grignard reagents reaction with carbonyl compounds

Homoenolates reaction with carbonyl compounds

Hydrazones reaction with carbonyl compounds

Hydride shifts reactions with carbonyl compounds

Hydroxylamine, reaction with carbonyl compounds

Iodides reactions with carbonyl compounds

Iron, carbonyl compounds reaction with base

Isoprene reactions with carbonyl compounds

Isoquinoline reactions with carbonyl compounds

Ketenes reaction with carbonyl compounds

Lanthanide homoenolates reactions with carbonyl compounds

Lithium dialkylcuprates reactions with carbonyl compounds

Lithium, 1-phenylseleno-l-thioalkylreactivity reactions with carbonyl compounds

Lithium, 1-seleno-1-silylalkylreactivity reactions with carbonyl compounds

Lithium, a-selenoalkylacyl anion equivalents reactions with carbonyl compounds

Lithium, a-selenoalkylnucleophilicity reactions with carbonyl compounds

Lithium, a-selenoallylambident reactivity reactions with carbonyl compounds

Lithium, a-selenocyclopropylreactivity reactions with carbonyl compounds

Magnesium bromide allylstannane reaction with carbonyl compounds

Methanesulfonic acid reactions with carbonyl compounds

Methanethiol, phenyldianions reactions with carbonyl compounds

Nickel sulfide silane reaction with carbonyl compounds

Organocadmium reagents reactions with carbonyl compounds

Organochromium reagents reactions with carbonyl compounds

Organolithium reagents reactions with carbonyl compounds

Organolithiums reaction with carbonyl compounds

Organomagnesium reagents reactions with carbonyl compounds

Organometallic compounds, reactions with carbonyls

Organosilanes reactions with carbonyl compounds

Organostannanes reactions with carbonyl compounds

Organotin compounds reactions with carbonyls

Organotitanium reagents reactions with carbonyl compounds

Organozinc reagents reactions with carbonyl compounds

Oxazoline, 2-alkylmetallated achiral reactions with carbonyl compounds

Phenylhydrazine reaction with carbonyl compounds

Photochemical cycloaddition reactions of carbonyl compounds with alkenes

Pinacol coupling reactions with carbonyl compounds

Propargylic acetates reactions with carbonyl compounds

Propionic acid reactions with carbonyl compounds

Propionic acid, 3- dianions reactions with carbonyl compounds

Propyne, l,3-bis dilithium anion reaction with aliphatic carbonyl compounds

Pyrrole, 2,5-bis reaction with carbonyl compounds

Reaction of carbonyl compounds with sulfur tetrafluoride

Reaction of stabilized carbanions with carbonyl compounds

Reaction with Carbonyl Compounds 2 Imines

Reactions of Carbonyl Compounds with Heteroatom Nucleophiles

Reactions of Carbonyl Compounds with Other Carbon Nucleophiles

Reactions of Carbonyl Compounds with a-Trimethylsilylcarbanions

Reactions of Co-ordinated Carbonyl Compounds with Nucleophiles

Reactions of Organolithiums with Carbonyl Compounds

Reactions with Chiral Non-Racemic Carbonyl Compounds

Reactions with Prochiral Carbonyl Compounds

Reactions with a, 3-Unsaturated Carbonyl Compounds

Reactions with carbonyl compounds aromatic aldehydes

Reactions with carbonyl compounds ketones

Reactions with carbonyl compounds mechanism

Reactions with carbonyl compounds olefin yields

Reactions with carbonyl compounds product isomerization

Rhodium, chlorotris catalyst silane reaction with carbonyl compounds

Schmidt reactions with carbonyl compounds

Selenides, p-hydroxyalkyl reactions with carbonyl compounds

Selenones, a-metalloalkyl reactions with carbonyl compounds

Selenonium ylides reactions with carbonyl compounds

Selenoxides, a-metalloalkyl reactions with carbonyl compounds

Selenoxides, a-metallovinyl reactions with carbonyl compounds

Silane, vinylepoxidation reaction with carbonyl compounds

Silanes reaction with carbonyl compounds

Silanes, allenyl annulations reactions with a,p-unsaturated carbonyl compounds

Silanones reactions with carbonyl compounds

Silyl enol ethers reactions with carbonyl compounds

Sodium bisulfite, reaction with carbonyl compounds

Stannanes reactions with carbonyl compounds

Stereoelectronics reactions of chiral carbonyl compounds with

Subject reactions with carbonyl compounds

Sulfoxide, benzyl f-butyl reactions with carbonyl compounds

Sulfoxide, methyl p-tolyl reactions with carbonyl compounds

Sulfoxides, a-halo reactions with carbonyl compounds

Sulfoxides, alkyl aryl reactions with carbonyl compounds

Sulfoxides, allyl p-tolyl reactions with carbonyl compounds

Sulfur ylides reactions with carbonyl compounds

The Reactions of Carbonyl Compounds with Hydride Ion

Thioanisole reaction with carbonyl compounds

Titanium complexes reactions with carbonyl compounds

Titanium tetrachloride allylstannane reactions with carbonyl compounds

Titanium tetrachloride reactions with carbonyl compounds

Titanium, ally 1heterosubstituted reactions with carbonyl compounds

Titanium, allylheterosubstituted reactions with carbonyl compounds

Titanium, methyl reactions with carbonyl compounds

Titanium, trichloromethylproperties reaction with carbonyl compounds

Titanium, tris methylproperties reaction with carbonyl compounds

Tosylates reactions with carbonyl compounds

Unsaturated carbonyl compounds reaction with organocopper reagents

With Carbonyl Compounds

Ylides reactions with carbonyl compounds

Ynamines reactions with carbonyl compounds

Zirconium reagents, allylic reaction with carbonyl compounds

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