Notes. Derivatives of Flourine. XIII. Formation of 9-Arylimino Compounds in the Presence of Boron Triflouride.

Taylor, Murray E.; Fletcher, T. Lloyd

doi:10.1021/jo01062a605

Cited by 25 publications

(5 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The sterically hindered amino group was prepared as follows: mesidine (mesitylenamine) was allowed to react with fluorenone in the presence of boron trifluoride etherate [4] at 150°C under fusion conditions to give N-9-fluorenylidenemesitylenamine 3 in 84% yield. The compound 3 thus obtained was reduced to the corresponding amine 4 by LiAlH4 (87% yield).…”

Section: Resultsmentioning

confidence: 99%

“…The compound 3 thus obtained was reduced to the corresponding amine 4 by LiAlH4 (87% yield). Then the diphosphenes bearing the (9-fluoreny1)mesitylamino group were prepared as follows.…”

Section: Resultsmentioning

confidence: 99%

“…However, addition of a catalytic amount of 1,8-diazabicyclo[5. 4.O]undec-7-ene (DBU) activated the sulfurization reaction to give the thiadiphosphirane 6b. Since formation of the intermediary diphosphene sulfide [9] has not been observed during the sulfurization reaction, monitored by 31P NMR spectroscopy, the isomerization of the diphosphene sulfide seems to be rapid in this captodative diphosphene system.…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Preparation and properties of some stable captodative diphosphenes carrying the N‐(9‐fluorenyl)‐N‐mesitylamino group as an electron‐donating new sterically protecting auxiliary

Abe

Toyota

Yoshifuji

1993

Heteroatom Chemistry

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

“…The compound 3 thus obtained was reduced to the corresponding amine 4 by LiAlH4 (87% yield). Then the diphosphenes bearing the (9-fluoreny1)mesitylamino group were prepared as follows.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Preparation and properties of some stable captodative diphosphenes carrying the N‐(9‐fluorenyl)‐N‐mesitylamino group as an electron‐donating new sterically protecting auxiliary

Abe

Toyota

Yoshifuji

1993

Heteroatom Chemistry

View full text Add to dashboard Cite

show abstract

“…A milder method, especially for the synthesis of fluorenone-derived imines, uses 0.16 equivalents of boron trifluoride-diethyl ether complex as a catalyst. [163] In the case of the synthesis of imines derived from optically active cycloalkanones, azeotropic distillation with toluene in the presence of 5% of the stoichiometric amount of dibutyltin dichloride might limit the level of epimerization. [164] Other possible catalysts include phenol, acetic acid, trifluoroacetic acid, and phosphonic acid ion-exchange resin.…”

Section: Nhr 3 Homentioning

confidence: 99%

Product Class 7: Imines

Padwa¹,

Bellus²

2005

Category 4. Compounds With Two Carbon Heteroatom Bonds

View full text Add to dashboard Cite

Compounds with the general structure R 1 R 2 C=NR 3 , referred to as imines, were first obtained by Schiff via condensation of ketones and aldehydes with primary amines. Therefore, the condensation products are also called Schiff bases. In addition, the nominations azomethine, ketimine (derived from ketones), aldimine (derived from aldehydes), and anil (derived from anilines) are in use. It is recommended that the terms imine(s), ketimine(s), or aldimine(s) are used, rather than Schiff base(s) or azomethine(s).Since imines have to be considered as analogues of carbonyl compounds, many of the chemical properties are similar to the latter. Imines are used in new C-C bond formations, and reactions with electrophiles (e.g., aldehydes, alkyl halides), and the C=N moiety can undergo nucleophilic reactions. Generally, imines are very useful compounds in organic synthesis, as they are used in several syntheses of aza-heterocyclic compounds. Most imines are stable in an alkaline medium and therefore can be dried over potassium hydroxide. In diluted acid, however, they are easily hydrolyzed. In many cases intermediary imines cannot be isolated because of their lability. The presence of a C=N bond creates the possibility for E/Z isomerism (syn/anti). It has been recognized that such geomet-

show abstract

“…To shift the equilibrium to the product side, higher temperatures, Increased reaction times, and the use of a catalyst are generally required. Also, removal of water during the reaction greatly enhances product formation (4,5). (See ref [6][7][8][9][10][11] for related dpk information.)…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new multidentate ligands. Carbonyl addition reactions of di-2-pyridyl ketone

Ortego¹,

Meynig²

1986

J. Chem. Eng. Data

View full text Add to dashboard Cite

Ethyienedlamlne and 1,3-dlamlnopropane add slowly to the carbonyl group of di-2-pyridyl ketone (dpk) to form the compounds (py)2C(OH)NHCH2CH2NHC(OH)(py)2 and (py)2C(OH)NHCH2CH2CH2NHC(OH)(py)2, respectively (py = 2-pyrldyl). Under reflux conditions In benzene, using boron trlfluortde etherate as a catalyst, dpk adds to ethyienedlamlne, 1,3-dlamlnopropane, and 1,2-diamlnopropane (with loss of H20) to form the Schlff bases (py)2C=NCH2CH2N=C(py)2, (py)2C=NCH2CH2CH2N=C(py)2, and (py)2C=NCH2CH(CH3)N=C(py)2, respectively. These new multidentate ligands were characterized by elemental analysis and Infrared, NMR, and thermogravlmetric techniques.

show abstract

Notes. Derivatives of Flourine. XIII. Formation of 9-Arylimino Compounds in the Presence of Boron Triflouride.

Cited by 25 publications

References 0 publications

Preparation and properties of some stable captodative diphosphenes carrying the N‐(9‐fluorenyl)‐N‐mesitylamino group as an electron‐donating new sterically protecting auxiliary

Preparation and properties of some stable captodative diphosphenes carrying the N‐(9‐fluorenyl)‐N‐mesitylamino group as an electron‐donating new sterically protecting auxiliary

Product Class 7: Imines

Synthesis of new multidentate ligands. Carbonyl addition reactions of di-2-pyridyl ketone

Contact Info

Product

Resources

About