Untitled

Kantlehner, Willi; Vettel, Markus; Gissel, Alexander; Haug, Erwin; Ziegler, Georg C.; Ciesielski, Michael; Scherr, Oliver; Haas, Richard

doi:10.1002/(sici)1521-3897(200003)342:3<297::aid-prac297>3.3.co;2-o

Cited by 8 publications

(12 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[7,8] This reaction is useful for the formylation of a wide range of substrates, including unsubstituted and alkyl-substituted aromatics, aromatic ethers, tertiary aromatic amines, fused aromatic rings, and thiophenes. Scheme 1.…”

Section: Formamide Derivatives As Formylating Agentsmentioning

confidence: 99%

“…[8] In an improved method, 2 can be prepared from triformamide and sodium diformamide [13,14] in 80% yield. [8,15] Tris(diformylamino)methane (2) is a stable, high-melting (142°C), nonhygroscopic, and nonetching compound. The compound is nearly odorless and easy to handle.…”

Section: Formylations With Tris(diformylamino)methanementioning

confidence: 99%

“…In the presence of (strong) Lewis acids, it is capable of formylating activated arenes. [8,15] The efficiency of 2 as a formylating agent is higher than that of triformamide (1), since up to three out of the seven formyl groups in 2 can be used synthetically, whereas 1 can transfer only one of its three formyl groups.…”

Section: Formylations With Tris(diformylamino)methanementioning

confidence: 99%

See 2 more Smart Citations

New Formylating Agents − Preparative Procedures and Mechanistic Investigations

et al. 2001

Self Cite

View full text Add to dashboard Cite

The reactivity of new formylating agents related to formamide has been investigated both experimentally and theoretically. The reaction in 1,2-dichloroethane between tris(diformylamino)methane (2) and several arenes, catalyzed by AlCl 3 or BCl 3 , was shown to proceed in good yields to afford the corresponding para-substituted aldehydes. The nature of the active electrophilic species was also investigated theoretically. Thus, the relative stability of the O-and N-protonated forms, as well as those of AlCl 3 adducts, of several formylat-

show abstract

Section: Formamide Derivatives As Formylating Agentsmentioning

confidence: 99%

Section: Formylations With Tris(diformylamino)methanementioning

confidence: 99%

Section: Formylations With Tris(diformylamino)methanementioning

confidence: 99%

See 1 more Smart Citation

New Formylating Agents − Preparative Procedures and Mechanistic Investigations

et al. 2001

Self Cite

View full text Add to dashboard Cite

show abstract

“…Mechanistische Studien zu derartigen Reaktionen liegen vor [20]. Schema 2. In mehreren Arbeiten sowie einem Übersichts-artikel [21] haben wir über Lewis-Säure-induzierte Aromatenformylierungen mit Hilfe von Triformamid (1) [22], Tris(diformylamino)methan ("Formyl-aalen") (2) [23] und N, N, N , N -Tetraformylhydrazin (3) [24] sowie Tris(dichlormethyl)amin (4) berichtet.…”

Section: Introductionunclassified

Orthoamide, LXIV [1]. Aromatenformylierungen mit Tris(dichlormethyl)amin und Oligoformylamin-Derivaten in Gegenwart von Supersäuren / Orthoamides, LXIV [1]. Formylation of Aromatic Compounds by Tris(dichloromethyl)amine and Oligoformylamine Derivatives in the Presence of Superacids

Kantlehner

Leonhardt

Ziegler

et al. 2007

Zeitschrift Für Naturforschung B

Self Cite

View full text Add to dashboard Cite

Tris(dichloromethyl)amine (4), triformamide (1) and tris(diformylamino)methane ("formylaalen") (2) can be activated by addition of trifluoromethanesulfonic acid. The formylating systems thus formed transform activated aromatic compounds, such as toluene, anisole or 2,4-dimethoxybenzene to the corresponding aldehydes. The formylating ability of systems from 4 and superacids, such as FSO 3 H, FSO 3 H/SbF 5 , C 4 F 9 SO 3 H, and mixtures of aluminum chloride with C 4 F 9 SO 3 H and chlorosulfonic acid, respectively, is compared. In general, low reaction temperatures (−20 to −10 • C) are necessary to obtain aldehydes with acceptable to good yields. Remarkably, at higher temperatures (∼ 100 • C) compound 4 can also act as a formylating agent in the presence of suitable zeolites, as e. g. zeolite HBEA. Reaction mechanisms of the new formylation reactions are proposed.

show abstract

“…During our studies on the formylation of aromatic compounds [1,8,9] we became interested in aryl formates as starting compounds for aromatic alde hydes via the Fries rearrangement. The results of these studies will be the subject of a forthcoming paper.…”

Section: Introductionmentioning

confidence: 99%

Orthoamides, LVI [1]. A New Method of Wide Scope for the Preparation of Aryl Formates

Ziegler

Kantlehner

2001

Zeitschrift Für Naturforschung B

Self Cite

View full text Add to dashboard Cite

Aryl Formates, Formylation, HydroxyarenesAryl formates 4a-u, 6 , 8 , 10, 12, 14, 16, 18, 20, 22, 24, 26 are prepared by formylation of hydroxyarenes 3a-u, 5, 7, 9, 11, 13, 15, 17, 19, 21, 23, 25 with /V,Af-diformylacetamide (1) or triformamide (2), respectively, in fairly good yields. The reactions can be catalyzed by sodium diformamide or praseodymium(III) triflate. The thiolformate 28 was obtained analogously from 1-thionaphthol (27).

show abstract

Untitled

Cited by 8 publications

References 0 publications

New Formylating Agents − Preparative Procedures and Mechanistic Investigations

New Formylating Agents − Preparative Procedures and Mechanistic Investigations

Orthoamide, LXIV [1]. Aromatenformylierungen mit Tris(dichlormethyl)amin und Oligoformylamin-Derivaten in Gegenwart von Supersäuren / Orthoamides, LXIV [1]. Formylation of Aromatic Compounds by Tris(dichloromethyl)amine and Oligoformylamine Derivatives in the Presence of Superacids

Orthoamides, LVI [1]. A New Method of Wide Scope for the Preparation of Aryl Formates

Contact Info

Product

Resources

About