The Schmidt Reaction Applied to Aldehydes and Epoxides<sup>1</sup>

McEwen, William E.; Conrad, Walter E.; VanderWerf, Calvin A.

doi:10.1021/ja01125a010

Cited by 52 publications

(21 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As shown in Scheme 3, the bis-cyano derivative 14 was prepared by palladium-catalyzed Suzuki coupling of 13 with 4-bromobenzonitrile, whereas the photochromic compound 16 was prepared from the bis-aldehyde 15 by a modification of the Schmidt reaction. [30] [9±14] As shown in Table 1 the open forms of 1 ± 5 show absorptions bands with l max values between 209 and 378 nm, whereas the highly colored closed forms 1 c ± 5 c display a typical broad absorption band in the visible region at wavelengths between 604 nm (4 c) and 632 nm (2 c).…”

Section: Abstract In Frenchmentioning

confidence: 99%

Optical Switching and Fluorescence Modulation Properties of Photochromic Metal Complexes Derived from Dithienylethene Ligands

1999

View full text Add to dashboard Cite

Organic photochromic systems represent a starting point for the preparation of light-triggered molecular switching devices. The novel dithienylethene-tungsten (1,2), rhenium (3,4), and ruthenium (5) complexes were synthesized from their parent ligands. The biscyano photochromic complexes 14 and 16 were also prepared although their metallic complexes could not be isolated. All the compounds described exhibited pronounced photochromic proper- forms when excited at wavelengths (240 nm) that almost did not affect the state of the system. Finally the closed form of product 5, prepared from the closed form of its parent ligand, was photochemically stable. Thus, the molecules 1 ± 5 represent two kinds of nondestructive read-out models.

show abstract

Section: Abstract In Frenchmentioning

confidence: 99%

Optical Switching and Fluorescence Modulation Properties of Photochromic Metal Complexes Derived from Dithienylethene Ligands

1999

View full text Add to dashboard Cite

show abstract

“…IR (CH,CI,): 3610 w , 3060 w , 2970 s, 2970 s, 2930s, 1680msh, 1665s, 1615m, 1470m, 1435m, 1380s, 1360m, 1320m, 1155m, 1090m, 1020s,960s,900s. ( 4 R*, SS*)-2,2,2-Trirnethoxy-4,S-diphenyl-l, 3,2 15-oxuzaphospholidin (16). IR (CH,CI,): 3460 m, 3020 m, 2940m, 2900m, 2830m, 1590w, 1485m, 1445m, 1365m, 1345 2950m,2900m,2840m, 1590w, 1485m, 1445m, 1370m, 1310m, 1220m, 1170m, 1080s, IOSOs, (4 R*, S S* j -2,2,2-Trimethoxy-4,5-tetramethylen-l,3,2 15-oxazuphospholidin ( = (3 aR*, 7aR* j- 2,2,4,5,6,7, [(2,6,6-Trimethylcyclohexl-enyl)methylimido]phosphorsiiure-trimeth.vlester (12). Analog zur Herstellung von 11 werden 1,35 g (7,5 mmol (Benzylimidojphosphorsuure-triathylester (13).…”

Section: Experimenteller Teilmentioning

confidence: 99%

Umsetzung von 2‐Azidoalkoholen mit Trialkylphosphiten Bildung von Aziridinen und Amidophosphorsäureesten via Imidophosphorsäureester und 1,3,2λ⁵‐Oxazaphospholidine

Willeit

Müller

Péringer

1983

Helvetica Chimica Acta

View full text Add to dashboard Cite

HELVETICA CHIMICA Fasc. 8 (1 983) -Nr. 246 2467 246. Umsetzung von 2-Azidoalkoholen mit Trialkylphosphiten Bildung yon Aziridinen und Amidophosphorsaureestern via Imidophosphorsaureester und 1,3,2 I '-Oxazaphospholidine van Armin Willeit ') und Reaction of ZAzidoalcohols with Trialkylphosphites. Formation of Aziridines and Amidophosphates via lmidophosphates and 1,3,2 A5-Oxazaphospholidines SummaryThe 2-azidoalcohols 1 and 2 react with trialkyl phosphites to trialkyl (2-hydroxy-alky1)imidophosphates 10,14, and 15 respectively, whereas the 2-azidoalcohols 3-7 yield the 2,2,2-trialkoxy-1,3,2 15-oxazaphospholidines 16-22 under the same reaction conditions (Scheme 2 ) . The dialkyl(2-hydroxyalkyl)amidophosphates 23,25, and 27-34 are obtained by the reaction of 10, and 14-22 with water (Scheme 3 and 4 ) . By reaction with alcohols, however, both the imidophosphates 10, 14, and 15 and the 1,3,2i5-oxazaphospholidines 16-22 are transformed to aziridines 24,26, and 35-38 (Scheme 5). The reactions of the imidophosphates seem to proceed via 1,3,2 i5-oxazaphospholidines. Auswahl derSubstrate. -Trimethylphosphit wurde trotz seines unangenehmeren Geruches Triathylphosphit vorgezogen, da es bei vergleichbarer Reaktivitat gegenuber Aziden [2] zu einfacheren 'H-NMR-und 13C-NMR-Spektren fuhrt; ob die Reaktion mit Triiithylphosphit gleichartig verlauft und zu homologen Produkten fuhrt, wurde durch die Umsetzung von drei reprasentativen Azidoalkoholen iiberpriift. Als 2-Azidoalkohole wurden die Verbindungen 1 [5], 2 [5], 3 [6], 4 [6], 5 [7], 6 [8] und 7 [9] (Schema 2) ausgewahlt, die primare, sekundare oder tertiare Alkohol-und Azid-Schema 2 1 2 14 5 18 7 2 0

show abstract

“…Thus McEwen et al 59 and later Smith and Antoniades 60 supposed that, by analogy with ketones, aldehydes react in the protonated form with hydrogen azide; the resultingprotonated azidoalkanol (I) loses water to give the iminodiazonium ion (II), which is subsequently converted into the reaction products:…”

Section: Mechanism Of Reaction Of Aldehydes With Hydrogen Azidementioning

confidence: 99%

“…Thus McEwen et al 59 investigated the action of hydrogen azide on a series of substituted benzaldehydes in the presence of sulphuric acid. They showed that the yields of formamides and nitriles can vary within wide limits depending on the acid concentration.…”

Section: Applications Of Reactionmentioning

confidence: 99%

Schmidt Reaction with Aldehydes and Carboxylic Acids

Koldobskii¹,

Островский²,

Gidaspov³

1978

Russ. Chem. Rev.

View full text Add to dashboard Cite

The Schmidt Reaction Applied to Aldehydes and Epoxides¹

Cited by 52 publications

References 1 publication

Optical Switching and Fluorescence Modulation Properties of Photochromic Metal Complexes Derived from Dithienylethene Ligands

Optical Switching and Fluorescence Modulation Properties of Photochromic Metal Complexes Derived from Dithienylethene Ligands

Umsetzung von 2‐Azidoalkoholen mit Trialkylphosphiten Bildung von Aziridinen und Amidophosphorsäureesten via Imidophosphorsäureester und 1,3,2λ⁵‐Oxazaphospholidine

Schmidt Reaction with Aldehydes and Carboxylic Acids

Contact Info

Product

Resources

About

The Schmidt Reaction Applied to Aldehydes and Epoxides1

Cited by 52 publications

References 1 publication

Optical Switching and Fluorescence Modulation Properties of Photochromic Metal Complexes Derived from Dithienylethene Ligands

Optical Switching and Fluorescence Modulation Properties of Photochromic Metal Complexes Derived from Dithienylethene Ligands

Umsetzung von 2‐Azidoalkoholen mit Trialkylphosphiten Bildung von Aziridinen und Amidophosphorsäureesten via Imidophosphorsäureester und 1,3,2λ5‐Oxazaphospholidine

Schmidt Reaction with Aldehydes and Carboxylic Acids

Contact Info

Product

Resources

About

The Schmidt Reaction Applied to Aldehydes and Epoxides¹

Umsetzung von 2‐Azidoalkoholen mit Trialkylphosphiten Bildung von Aziridinen und Amidophosphorsäureesten via Imidophosphorsäureester und 1,3,2λ⁵‐Oxazaphospholidine