scholarly journals Reactions of Cyclopropanone Acetals with Alkyl Azides:  Carbonyl Addition versus Ring-Opening Pathways

2007 ◽  
Vol 72 (25) ◽  
pp. 9439-9447 ◽  
Author(s):  
Scott Grecian ◽  
Pankaj Desai ◽  
Craig Mossman ◽  
Jennifer L. Poutsma ◽  
Jeffrey Aubé
Keyword(s):  
Ring Opening ◽  
Alkyl Azides ◽  
Carbonyl Addition

scholarly journals Sulfonium Ion-Promoted Traceless Schmidt Reaction of Alkyl Azides

2021 ◽  
Author(s):  
Bayu Ardiansah ◽  
Hiroki Tanimoto ◽  
Takenori Tomohiro ◽  
Tsumoru Morimoto ◽  
Kiyomi Kakiuchi
Keyword(s):  
Ring Opening ◽  
One Pot ◽  
Schmidt Reaction ◽  
Alkyl Azides ◽  
Sulfonium Ions ◽  
Bond Scission ◽  
Imine Compounds ◽  
Tertiary Alkyl

Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction showcased ring-opening, -expansion, and one-pot further conversion of the substrates as well as the application with C-H azidation.

scholarly journals Sulfonium Ion-Promoted Traceless Schmidt Reaction of Alkyl Azides

2021 ◽  
Author(s):  
Bayu Ardiansah ◽  
Hiroki Tanimoto ◽  
Takenori Tomohiro ◽  
Tsumoru Morimoto ◽  
Kiyomi Kakiuchi
Keyword(s):  
Ring Opening ◽  
One Pot ◽  
Schmidt Reaction ◽  
Alkyl Azides ◽  
Sulfonium Ions ◽  
Bond Scission ◽  
Imine Compounds ◽  
Tertiary Alkyl

Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction showcased ring-opening, -expansion, and one-pot further conversion of the substrates as well as the application with C-H azidation.

Formation of a cyclic tetrahedral intermediate by the addition of water to 2-methyl-4H- 3,1-benzoxazine followed by ring opening to 2-aminobenzyl acetate and 2-acetylaminobenzyl alcohol; pH-dependence of rate of reaction and product ratio

1999 ◽  
Vol 77 (5-6) ◽  
pp. 1035-1041 ◽  
Author(s):  
Wendy J Dixon ◽  
Frank Hibbert
Keyword(s):  
Ring Opening ◽  
Ph Dependence ◽  
Kinetic Studies ◽  
Ph Profile ◽  
Hydroxide Ion ◽  
Product Ratio ◽  
Tetrahedral Intermediate ◽  
Rate Of Reaction ◽  
Buffer Base ◽  
Carbonyl Addition

Kinetic studies have shown that addition of water to protonated 2-methyl-4H-3,1-benzoxazine occurs to give a cyclic tetrahedral carbonyl addition intermediate. At pH <5, the intermediate is protonated and reacts to 2-aminobenzyl acetate, whereas at pH >7.5, the unprotonated intermediate collapses to give 2-acetylaminobenzyl alcohol. The former reaction is catalysed by buffer base but the latter is uncatalysed. At pH 9-12, reaction of hydroxide ion with protonated 2-methyl-4H-3,1-benzoxazine to give 2-acetylaminobenzyl alcohol becomes important, and at pH >12, the same product is formed by reaction of hydroxide ion with unprotonated 2-methyl-4H-3,1-benzoxazine.Key words: mechanism, addition, tetrahedral intermediate, hydrolysis, pH profile.

scholarly journals Sulfonium Ion-Promoted Traceless Schmidt Reaction of Alkyl Azides

2021 ◽  
Author(s):  
Bayu Ardiansah ◽  
Hiroki Tanimoto ◽  
Takenori Tomohiro ◽  
Tsumoru Morimoto ◽  
Kiyomi Kakiuchi
Keyword(s):  
Ring Opening ◽  
One Pot ◽  
Schmidt Reaction ◽  
Alkyl Azides ◽  
Sulfonium Ions ◽  
Bond Scission ◽  
Imine Compounds ◽  
Tertiary Alkyl

Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction showcased ring-opening, -expansion, and one-pot further conversion of the substrates as well as the application with C-H azidation.

Amino-functional polyethers: versatile, stimuli-responsive polymers

2020 ◽  
Vol 11 (24) ◽  
pp. 3940-3950 ◽  
Author(s):  
Patrick Verkoyen ◽  
Holger Frey
Keyword(s):  
Ring Opening ◽  
Review Article ◽  
Stimuli Responsive ◽  
New Class ◽  
Stimuli Responsive Polymers ◽  
Responsive Polymers

Amino-functional polyethers have emerged as a new class of “smart”, i.e. pH- and thermoresponsive materials. This review article summarizes the synthesis and applications of these materials, obtained from ring-opening of suitable epoxide monomers.

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