The reaction between 2,3-Diphenyl-2H-azirine and Phenyldiazomethane

1973 ◽  
Vol 26 (11) ◽  
pp. 2547 ◽  
Author(s):  
JH Bowie ◽  
B Nussey ◽  
AD Ward
Keyword(s):  
Double Bond ◽  
Good Yield ◽  
Alternative Synthesis

The reaction between 2,3-diphenyl-2H-azirine and phenyldiazomethane produces the stable 1-azido-1,2,3-triphenylprop-1-ene in good yield. The structure is confirmed by an alternative synthesis which indicates that the double bond has the E-configuration.

TRYPTAMINES, CARBOLINES, AND RELATED COMPOUNDS: PART X. AN ALTERNATIVE SYNTHESIS, AND THE NITRATION, OF δ-CARBOLINE

1962 ◽  
Vol 40 (5) ◽  
pp. 864-869 ◽  
Author(s):  
R. A. Abramovitch ◽  
K. A. H. Adams
Keyword(s):  
Dipole Moment ◽  
Molecular Orbital ◽  
Good Yield ◽  
Molecular Orbital Calculations ◽  
Alternative Synthesis ◽  
Fischer Cyclization ◽  
Nitro Derivatives ◽  
Related Compounds ◽  
Predominant Product

δ-Carboline, together with β-carboline, has been synthesized in reasonably good yield by the Fischer cyclization of cyclohexanone 3-pyridylhydrazone followed by dehydrogenation of the separated tetrahydro derivatives. The isomer ratios of products formed in this and similar reactions are discussed. Nitration of δ-carboline gives a mixture of the 6- and 8-nitro derivatives, the latter being the predominant product. The magnitude of the dipole moment of δ-carboline is appreciably higher than that predicted from molecular orbital calculations (15).

Model Compounds Related to Saquayamycin. Attempts to Oxygenate the A/B Ring Junction

2002 ◽  
Vol 55 (5) ◽  
pp. 343 ◽  
Author(s):  
M. A. Apponyi ◽  
J. H. Bowie ◽  
B. W. Skelton ◽  
A. H. White
Keyword(s):  
Double Bond ◽  
Maleic Anhydride ◽  
Good Yield ◽  
Ring Opening ◽  
Diels Alder ◽  
Aromatic System ◽  
Model Compounds ◽  
Similar Treatment ◽  
Ring Junction

The aim of this project was to attempt to find a method for introducing the cis-dihydroxyl substitution at the A/B-ring junction of model compounds related to the saquayamycins. The Diels-Alder reactions of maleic anhydride and bromomaleic anhydride with 5,5-dimethyl-3-vinylcyclohexa-1,2-dienyl acetate gave the two required endo-adducts in good yield, namely (octahydrobenzo[e]isobenzofuran-9-yl acetate (6) and (octahydrobenzo[e]isobenzofuran-9-yl acetate (9). Each of these was converted into the B-ring mono-epoxide, namely (H-benzo[e]oxireno-2,3-furan-1-yl acetate (7) and a mixture of two racemic diastereoisomers of 9a-bromo-3,3-dimethyl-7,9-dioxoperhydrobenzo[e]oxi- reno[2,3-f]isobenzofuran-1-yl acetate (12), respectively. It was then hoped to deprotonate both (7) and (12) at the 9a position in order to effect migration of the 8,9 double bond to the 9,9a position. Reaction of (7) with a mild base (pyridine) did not effect any reaction. Similar treatment of (12) did remove the 9a proton, but it also effected ring opening of the epoxide, followed by dehydration and dehydrobromination to give an excellent (but unwanted) yield of the aromatized system (±)-7,7-dimethyl-1,3-dioxo-1,3,5,7-tetrahydrobenzo (e]isobenzofuran-9-yl acetate. Dehydrobromination of (9), and deprotonation of the 9a position, similarly formed the aromatic system (e]isobenzofuran-9-yl acetate (11) in good yield.

Synthesis of New Pyrazolenines and Cyclopropenyl Alcohols Directly from Propargyl Alcohols

2005 ◽  
Vol 2005 (5) ◽  
pp. 289-292 ◽  
Author(s):  
Naceur Hamdi ◽  
Pierre Henry Dixneuf ◽  
Youssef Arfaoui ◽  
Ezzeddine Haloui
Keyword(s):  
Double Bond ◽  
Good Yield ◽  
Dipolar Cycloaddition ◽  
Propargylic Alcohols ◽  
Propargyl Alcohols

The 1,3-dipolar cycloaddition of 2-diazopropane 1 to propargylic alcohols is regioselective and leads to 3H-pyrazoles 3 in good yield. The surprising formation of the tetrasubstitued pyrazolenine 4c from HC=CCH2OH and 1 can be explained via the 1,3-dipolar cycloadduct intermediate followed by a second cycloaddition of 1 to the C=C double bond and loss of dinitrogen. The photolysis of the antibacterial pyrazolenines 3 and 4 selectively gives α and β dimethylcyclopropenyl alcohols 5 and 6.

Studies on the reaction of nitric oxide with α,β-unsaturated hydrazones

2012 ◽  
Vol 90 (6) ◽  
pp. 510-516 ◽  
Author(s):  
Desuo Yang ◽  
Xiaolin Luo ◽  
Haiyun Zhu ◽  
Yaning Guo ◽  
Longmin Wu
Keyword(s):  
Nitric Oxide ◽  
Double Bond ◽  
Good Yield ◽  
Electrophilic Addition ◽  
Carbon Double Bond ◽  
High Stereoselectivity

α,β-Unsaturated arylhydrazones (1) reacted with nitric oxide (NO) in the presence of a trace of oxygen to give α- (2a–2c, 2e, and 2f) or β-nitro (2d and 2g) unsaturated hydrazones in good yield and with high stereoselectivity. The reaction occurs most likely by an electrophilic addition of NO2 to the carbon–carbon double bond of 1 at its α- or β-position.

SYNTHESES AND POLYMERIZATION OF α-TRIMETHYLSILYL ACRYLIC MONOMERS

1963 ◽  
Vol 41 (12) ◽  
pp. 2977-2982 ◽  
Author(s):  
Ariel Ottolenghi ◽  
Mati Fridkin ◽  
A. Zilkha
Keyword(s):  
Free Radicals ◽  
Double Bond ◽  
Methyl Ester ◽  
Acrylic Acid ◽  
Anionic Polymerization ◽  
Good Yield ◽  
Steric Effect ◽  
Trimethylsilyl Group ◽  
Acrylic Monomers

α-Trimethylsilyl acrylic acid and its methyl ester were prepared in good yield starting from 1,2-dibromoethyltrimethylsilane. These monomers were polymerized with difficulty by free radicals to viscous polymers, but gave solid copolymers with styrene. The methyl ester was also a weak monomer in anionic polymerization. This non-reactivity is due to the steric effect of the α-trimethylsilyl group adjacent to the double bond.

Ozonolysis of Derivatives of Labda-8(17),14-dien-13-ol (Manool) and Their Conversion Into Large Ring Unsaturated Lactones

1988 ◽  
Vol 41 (5) ◽  
pp. 711 ◽  
Author(s):  
PK Grant ◽  
KL Chee ◽  
JS Prasad ◽  
MY Tho
Keyword(s):  
Double Bond ◽  
Good Yield ◽  
Spatial Relationship ◽  
Hydroxyl Group ◽  
Exocyclic Double Bond ◽  
Large Ring ◽  
Unsaturated Lactones ◽  
Derivatives Of

Dehydration of the unstable hydroperoxy ethers (4) and (6) formed on ozonolysis of the manool derivatives (2) and (5) resulted in the formation of the ten- membered unsaturated lactones (11) and (12) in good yield. The results of an investigation into the nature of the hydroxyl group and its spatial relationship to the exocyclic double bond in lactone formation are reported for other manool derivatives.

Preparation and transformations of allenic ketones and 3(2H)-furanones

1984 ◽  
Vol 62 (11) ◽  
pp. 2429-2434 ◽  
Author(s):  
Steven Wolff ◽  
William C. Agosta
Keyword(s):  
Double Bond ◽  
Carboxylic Acids ◽  
Good Yield ◽  
Osmium Tetroxide ◽  
Methyl Esters ◽  
Allene Oxide ◽  
Similar Treatment ◽  
Ruthenium Tetroxide ◽  
Swern Oxidation ◽  
Villiger Oxidation

Swern oxidation of allenic alcohols 7 and 10 gives the corresponding ketones 3 and 12. Reaction of 3 with ruthenium tetroxide yields the stable acyl ketene 17 and the acyloxy α-diketone 20 as well as pivalil (4). Formation of 20 by way of the 3(2H)-furanone 22 is suggested, since oxidation of 3 and 12 with osmium tetroxide followed by dehydration provides the corresponding furanones 22 and 26 in good yield. Epoxidation of 3 furnishes some 20 as well as 27 and 29, the first stable keto allene oxide and bisepoxide, respectively. On thermolysis 27 rearranges to furanone 22. The double bond of 22 is cleaved by peracid to form 20; similar treatment of 31a, b leads to cleavage of the double bond accompanied by Baeyer–Villiger oxidation, with formation of the carboxylic acids corresponding to methyl esters 33a, b as the major products.

scholarly journals Zur Reaktivität von C =N-Doppelbindungssystemen, III Eine einfache Olefinierungs-Reaktion / The Reactivity of the C=N-Double Bond System, III A Simple Olefination Reaction

1975 ◽  
Vol 30 (9-10) ◽  
pp. 755-759 ◽  
Author(s):  
Erich Ziegler ◽  
Walter Rüf ◽  
Johann G. Zwainz
Keyword(s):  
Double Bond ◽  
Acetic Anhydride ◽  
Good Yield ◽  
Succinic Anhydride ◽  
Propionic Anhydride ◽  
Double Bond System ◽  
Bond System ◽  
Cyclic Anhydrides

The reaction of benzylidene anilines with compounds having an activated CH,- or CH,-group in the presence of aliphatic or cyclic anhydrides (acetic anhydride, propionic anhydride or succinic anhydride) gives olefines in good yield.

scholarly journals Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones

2016 ◽  
Vol 12 ◽  
pp. 301-308 ◽  
Author(s):  
Ping Qian ◽  
Bingnan Du ◽  
Wei Jiao ◽  
Haibo Mei ◽  
Jianlin Han ◽  
...  
Keyword(s):  
Double Bond ◽  
Intramolecular Cyclization ◽  
Good Yield ◽  
Oxidative Reaction ◽  
Reaction Proceeds

An oxidative reaction for the synthesis of 4-alkyl-substituted dihydroisoquinolin-1(2H)-ones with N-allylbenzamide derivatives as starting materials has been developed. The radical alkylarylation reaction proceeds through a sequence of alkylation and intramolecular cyclization. The substituent on the C–C double bond was found to play a key role for the progress of the reaction to give the expected products with good chemical yields. Additionally, N-methacryloylbenzamides were also suitable substrates for the current reaction and provided the alkyl-substituted isoquinoline-1,3(2H,4H)-diones in good yield.

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