ortho-Formylation of oxygenated phenols

Akselsen, Øyvind W.; Skattebøl, Lars; Hansen, Trond Vidar

doi:10.1016/j.tetlet.2009.08.101

Cited by 36 publications

(19 citation statements)

References 155 publications

(184 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Fortunately the products are easily separated so that using the latter amine we were able to obtain 9b (58%) and 10 (15%) on a gram scale. We observed a similar effect of amine bulk on the chlorination selectivity with phenol 11 , which gave a 0.8:1, 1.8:1, 2.4:1, or 2.6:1 mixture of 12 13 and 13 14 with sulfuryl chloride and t -butylamine, dipropylamine, diisopropylamine, or 2,2,6,6-tetramethylpiperidine, respectively.…”

supporting

confidence: 56%

Syntheses of Chloroisosulochrin and Isosulochrin and Biomimetic Elaboration to Maldoxin, Maldoxone, Dihydromaldoxin, and Dechlorodihydromaldoxin

Snider

2011

Org. Lett.

View full text Add to dashboard Cite

An efficient synthesis of chloroisosulochrin was accomplished using a novel ortho-selective chlorination of a phenol with sulfuryl chloride and 2,2,6,6-tetramethylpiperidine as the key step. Further elaboration by a biomimetic route converted chloroisosulochrin to dihydromaldoxin, maldoxone (lactone formed by dehydration of dihydromaldoxin), and maldoxin and isosulochrin to dechlorodihydromaldoxin and dechloromaldoxin.

show abstract

supporting

confidence: 56%

Syntheses of Chloroisosulochrin and Isosulochrin and Biomimetic Elaboration to Maldoxin, Maldoxone, Dihydromaldoxin, and Dechlorodihydromaldoxin

Snider

2011

Org. Lett.

View full text Add to dashboard Cite

show abstract

“…2-(Hydroxymethyl)-4-methoxyphenol and 2-(hydroxymethyl)-5-methoxyphenol were prepared from 4-methoxyphenol and 5-methoxyphenol, respectively, using a published procedure. [27] Tin(IV) tert-butoxide, [24] tin(II) n-butoxide, [28] tin(II) acetate, [29] tin(IV) acetate, [30] tin(II) methoxide, [28] 2,2'-spirobi[4H-1,3,2-benzodioxasiline], [15,17] 2,2'-spirobi[4H-1,3,2-benzodioxastannine] (A), [13] 2,2'-spirobi[6-methyl-4H-1,3,2-benzodioxastannine] (B), [13] and 2,2'-spirobi[6-methoxy-4H-1,3,2-benzodioxastannine] (C) [13] were prepared according to literature procedures. Solid-state NMR measurements were performed at 9.4 T on a Bruker Avance 400 spectrometer equipped with double-tuned probes capable of magic angle spinning.…”

Section: Methodsmentioning

confidence: 99%

Tin Nanoparticles in Carbon/Silica Hybrid Materials by the Use of Twin Polymerization

et al. 2014

View full text Add to dashboard Cite

Simultaneous twin polymerization was used to synthesize hybrid materials composed of tin oxide, silica, and a phenolic resin starting from a mixture of 2,2′‐spirobi[4H‐1,3,2‐benzodioxasiline] (Si‐spiro) with either the tin(IV) alkoxides 2,2′‐spirobi[4H‐1,3,2‐benzodioxastannine] (A), 2,2′‐spirobi[6‐methyl‐4H‐1,3,2‐benzodioxastannine] (B), and 2,2′‐spirobi[6‐methoxy‐4H‐1,3,2‐benzodioxastannine] (C) or the novel tin(II) alkoxides tin(II)‐2‐(oxidomethyl)‐4‐methoxyphenolate (D) and tin(II)‐2‐(oxidomethyl)‐5‐methoxyphenolate (E). In addition, the twin polymerization of the twin monomer Si‐spiro in the presence of tin‐containing additives, such as Sn(OtBu)4, Sn(OnBu)2, Sn(OAc)4, and Sn(OAc)2, was investigated for comparison. The as‐prepared hybrid materials were characterized using solid‐state NMR spectroscopy (13C, 29Si, 119Sn) and high‐angle annular dark field scanning transmission electron microscopy, and were finally converted under Ar/H2 atmosphere at 600 °C to tin nanoparticles (10–200 nm) in porous carbon/silica hybrid materials (Sn/C/SiO2) with BET surface areas up to 352 m2 g−1.

show abstract

“…Numerous formylation methods were developed to prepare diverse aromatic aldehydes from corresponding phenols [6], such as the Duff reaction [7][8][9], Vilsmeier-Haack reaction [10][11][12], Reimer-Tiemann reaction [13][14][15], Gattermann-Koch reaction [16,17], Gattermann reaction [18,19], Rieche reaction [20][21][22], and paraformaldehyde/MgCl 2 reaction [23,24]. These methods possess their individual advantages, however, low ortho-selectivity of the most of these methods and poor yields sharply limited their application in industry [25].…”

Section: Introductionmentioning

confidence: 99%