ChemInform Abstract: AZOLE 74. MITT. CHEMISCHE EIGENSCHAFTEN VON SUBSTITUIERTEN TETRAMETHYLENISOXAZOLEN

Jacquier, Robert; Petrus, C.; Petrus, Francoise; Valentin, Michel

doi:10.1002/chin.197047329

Cited by 2 publications

(6 citation statements)

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“…Fractions 10-13 gave 29 mg (0.17 mmol, 35%) of 2-ethoxy-1 -phenylpropane (9), identified by NMR and GC-MS comparison with an authentic sample.12 Fractions 18-23 contained 178 mg of unreacted starting material. Fractions 25-28 yielded 20 mg (0.16 mmol, 31%) of benzaldehyde (10), identified by NMR and ir. Fractions 31-33 gave 11 mg (0.06 mmol, 12%) of 2-ethoxy-l-phenyl-l-propanol (11).…”

Section: Discussionmentioning

confidence: 99%

“…Fractions 10-13 produced 62 mg (0.35 mmol, 35%) of 2-ethoxy-1phenylpropane (9). Fractions 18-23 gave 35 mg (0.29 mmol, 29%) of benzaldehyde (10) and fractions 30-34 afforded 24 mg (0.12 mmol, 24%) of 2-ethoxy-l-phenyl-l-propanol (11).…”

Section: Discussionmentioning

confidence: 99%

“…Vycor-Filtered Irradiation of Benzaldehyde (10). Benzaldehyde (120 mg, 1.00 mmol) was irradiated for 0.25 hr and chromatographed according to the standard conditions described above.…”

Section: Discussionmentioning

confidence: 99%

“…The intermediacy of stilbene oxide (12) or its precursor 13 (X = O) in the formation of 9, 10, and 11 is clearly suggested by the fact that compounds 9-11 arise from irradiation of 128 in the same relative amounts as from 3. Also, photolysis of benzaldehyde (10) in ether produced 11, indicating 10 Irradiation of bis(diphenylmethyl) sulfide (4) produced no detectable amount of biphenyl, although diphenylmethane (5, 28%), 1,1,2,2-tetraphenylethane (7, 44%), and bis-(diphenylmethyl) disulfide (14%) were observed.…”

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confidence: 99%

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Comparison of photochemical reactions of (C6H5)2CHXCH(C6H5)2 (X = imino, methylene, oxygen, sulfur) systems

Binkley¹,

Chen²,

Hehemann³

1975

J. Org. Chem.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

“…Vycor-Filtered Irradiation of Benzaldehyde (10). Benzaldehyde (120 mg, 1.00 mmol) was irradiated for 0.25 hr and chromatographed according to the standard conditions described above.…”

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

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Comparison of photochemical reactions of (C6H5)2CHXCH(C6H5)2 (X = imino, methylene, oxygen, sulfur) systems

Binkley¹,

Chen²,

Hehemann³

1975

J. Org. Chem.

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“…For example amide 5 is produced along with acylated cyclic enamines 1 and 2 when this method is used. Production of amides from enamines by the reaction of acyl halides with enamines has been reported before [7], but this reaction involves different reagents and so follows a different mechanistic pathway. These amides are probably produced by way of initial formation of pseudobase 3 or 4 followed by elimination of amide 5 in a retro condensation reaction.…”

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confidence: 96%

Isomer Distribution of Succinylcyclohexenyl, Acetylcyclohexenyl and Acetylcyclopentenyl Enamines

Cook¹,

Folk

2008

LOC

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The isomeric distributions of some cyclohexenyl enamines substituted by succinyl or acetyl groups at either the 2-or 6-positions are reported as are the isomeric distributions of similarly substituted cyclopentenyl enamines. Correlation between the 13 C NMR chemical shifts in these enamines and isomer distribution is shown. Density functional molecular modeling is used to demonstrate resonance and electrostatic effects on isomeric distributions.One of the most common methods of synthesizing cyclohexenyl and cyclopentenyl enamines is to allow a cyclohexanone or a cyclopentanone compound to react with a secondary amine [1,2]. If the enamine is unsymmetrically substituted at the 2,6-positions (cyclohexenyl) or at the 2,5-positions (cyclopentenyl), two different isomers may be produced, namely tet and tri (Eq. 1) with the latter present as two different conformers in the cyclohexenyl case, tri ax (substituted X is pseudoaxial) and tri eq (substituted X is pseudoequatorial).We produced cyclohexenyl enamines with acetyl substituents in the 2-and 6-positions and cyclopentenyl enamines with acetyl substituents in the 2-and 5-positions in two different ways. They were synthesized by direct carbon acylation of the enamine [3,4] and by reaction of an acetylcycloalkanone with a secondary amine [5,6] (Scheme 1). We have found that the isomeric distributions of enaminoketones 1 and 2 are essentially the same for each of the two alternative methods of synthesis. We have further discovered that the second method (acetylcycloalkane with a secondary amine) also produces an amide. For example amide 5 is produced along with acylated cyclic enamines 1 and 2 when this method is used. Production of amides from enamines by the reaction of acyl halides with enamines has been reported before [7], but this reaction involves different reagents and so follows a different mechanistic pathway. These amides are probably produced by way of initial formation of pseudobase 3 or 4 followed by elimination of amide 5 in a retro condensation reaction. Further proof for this mechanism is shown by the appearance of significant amounts of simple cyclic ketones and simple enamines in the crude reaction products as determined by GC-MS. A similar reaction has been reported with the reaction of pyrrolidine with acetylacetone under microwave conditions [8]. The yields of amides represent the amount of alternate enaminoketone (with an exocyclic double bond due to attack of the acetyl carbonyl by the amine) which would have formed if the retro reaction to form amide 5 did not take place. + + 1 tet, n=1 1 tri, n=1 2 tet, n=0 2 tri, n=0 + + 3, n=1 4, n=0 5 + Scheme 1.The isomeric distributions of products for these reactions are given in Tables 1 and 2 along with the isomeric distribution of some previously unreported or erroneously reported enamines of 2-methyl-and 3-phenylcyclohexanones.The relative amounts of the isomers were determined by using 13 C NMR in CDCl 3 solvent with a long relaxation delay. The pseudo-equatorial and pseudo-axial configurational iden...

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ChemInform Abstract: AZOLE 74. MITT. CHEMISCHE EIGENSCHAFTEN VON SUBSTITUIERTEN TETRAMETHYLENISOXAZOLEN

Abstract: Der Versuch der Aromatisierung der Isoxazole (I) in Gegenwart von Pd/Koh le führt zu den Acylanilinen (III) (65‐75% Ausbeute).

Cited by 2 publications

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Comparison of photochemical reactions of (C6H5)2CHXCH(C6H5)2 (X = imino, methylene, oxygen, sulfur) systems

Comparison of photochemical reactions of (C6H5)2CHXCH(C6H5)2 (X = imino, methylene, oxygen, sulfur) systems

Isomer Distribution of Succinylcyclohexenyl, Acetylcyclohexenyl and Acetylcyclopentenyl Enamines

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