Notes- Preparation of Polyvinylamine Perchlorate.

Wolfrom, M. L.; Chaney, Alan

doi:10.1021/jo01063a624

Cited by 9 publications

(4 citation statements)

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“…Mp: 140-142 °C (lit. 18 142-144 °C). 1 H NMR (300 MHz, CDCl 3 ) δ ( ppm): 7.62-7.82 (m, 6H), 7.16 (d, J = 8.0 Hz, 2H), 4.32 (t, J = 5.4 Hz, 2H), 3.93 (t, J = 5.4 Hz, 2H), 2.32 (s, 3H).…”

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confidence: 99%

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Insights into the Pummerer synthesis of oxazolines

et al. 2016

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A rapid and simple method to access unnatural 2-substituted 5-thio oxazolines has been developed. This methodology is based on a Pummerer reaction followed by an intramolecular nucleophilic substitution, which changes the paradigm for the normal use of a base in Pummerer chemistry. We also provide a useful two-step method for the synthesis of the starting material and a mechanistic proposal based on experimental observations, which contests the previously proposed reaction pathway. The reaction proved to be general, and different substituents, such as alkyl, aryl, alkenyl and functionalized groups, can be used without a significant decrease in efficiency.

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“…Mp: 140-142 °C (lit. 18 142-144 °C). 1 H NMR (300 MHz, CDCl 3 ) δ ( ppm): 7.62-7.82 (m, 6H), 7.16 (d, J = 8.0 Hz, 2H), 4.32 (t, J = 5.4 Hz, 2H), 3.93 (t, J = 5.4 Hz, 2H), 2.32 (s, 3H).…”

Section: General Informationmentioning

confidence: 99%

“…1 H NMR (300 MHz, CDCl 3 ) δ ( ppm): 7.62-7.82 (m, 6H), 7.16 (d, J = 8.0 Hz, 2H), 4.32 (t, J = 5.4 Hz, 2H), 3.93 (t, J = 5.4 Hz, 2H), 2.32 (s, 3H). 13 (16), 117 (2), 104 (18), 91 (39), 77 (27), 65 (30), 50 (15).…”

Section: General Informationmentioning

confidence: 99%

Insights into the Pummerer synthesis of oxazolines

et al. 2016

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“…These products could be formed after the initial hydrolysis of 2 to bromoethylphthalamic acid (10). Nucleophilic displacement of bromo group by carboxyl, oxygen could yield 1 while 7 could be obtained by displacement of leaving group by amide oxygen.…”

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“…Isolation of 13 indicated formation of a small amount of phthalic anhydride on heating 7 as condensation of phthalic anhydride with 3 affords 13 (10).…”

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Alkaline Hydrolysis Products of N-Substituted Phthalimides

Hasan¹,

Abbas²

1975

Can. J. Chem.

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Products of alkaline hydrolysis of N-substituted phthalimides are described. Five isomeric compounds, 1,6-diketo-3,4,5,6-tetrahydro-1 H-2,5-benzoxazocine (1), 2-(o-carboxyphenyl)-Δ2 -oxazoline (7), 2-phthalimidoethanol (3), N-vinylphthalamic acid (8), and N-(o-carboxybenzoyl)-aziridine (9), are possible from the alkaline hydrolysis of 2-bromoethylphthalimide (2). Gabriel claimed in 1905 that 1 was formed on alkaline hydrolysis of 2 but later structure 7 was suggested for the product. The interest in the synthesis of 1 has led to a reinvestigation of this hydrolysis and structure 7 is confirmed for the initial product of the hydrolysis but it converts on warming during recrystallization into 1 which affords 3 on heating above melting point.Hydrolysis of 2-chloroethylphthalimide (4) and 2-phthalimidoethyl-p-toluenesulfonate (5) also afforded 7. Attempted preparation of 1 from intramolecular cyclization of 2-hydroxyethylphthalamic acid (11) was not successful and only 3 was obtained.Reaction of phthalic anhydride with 2-aminoethylsulfuric acid (14) at 150 ° afforded diphthalimidoethyl phthalate (13) instead of 2-phthalimidoethylsulfuric acid (6). Isolation of 13 indicates formation of 3 as an intermediate product in this reaction.

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Ethenylcarbamic Acid Benzyl Ester and Ethenylcarbamic Acid 1,1-Dimethylethyl Ester

Kamatani

2008

Encyclopedia of Reagents for Organic Synthesis

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Notes- Preparation of Polyvinylamine Perchlorate.

Cited by 9 publications

References 0 publications

Insights into the Pummerer synthesis of oxazolines

Insights into the Pummerer synthesis of oxazolines

Alkaline Hydrolysis Products of N-Substituted Phthalimides

Ethenylcarbamic Acid Benzyl Ester and Ethenylcarbamic Acid 1,1-Dimethylethyl Ester

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