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THE DEALKYLATION OF TERTIARY AMINES WITH THIOPHOSGENE AND ...

THE DEALKYLATION OF TERTIARY AMINES WITH THIOPHOSGENE AND ...

dealkylation of tertiary amines, and thus their conversion to secondary amines, has largely been replaced in recent years by the use of chloroformate esters [2]. The initial difficulties in the hydrolysis of the first formed carbamates (Scheme 1) was overcome to a significant extent by the use of 1-chloroethyl chloroformate [3], vinyl chloroformate [4], 2,2,2-trichloroethyl chloroformate [5 ...

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THE DEALKYLATION OF TERTIARY AMINES P-CHLOROPHENYL ...

THE DEALKYLATION OF TERTIARY AMINES P-CHLOROPHENYL ...

THE DEALKYLATION OF TERTIARY AMINES WITH P-CHLOROPHENYL CHLOROTHIONOFORMATE; A NEW DEALKYLATION AGENT OF TERTIARY AMINES M. Heidari, A. Afghan, Mehdi M. Baradarani Chemistry Department, Urmia University, Urmia 57135, Iran E-mail: [email protected] p-Chlorophenyl ...

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Archive of SID

Archive of SID

dealkylation of tertiary amines, and thus their conversion to secondary amines, has largely been replaced in recent years by the use of chloroformate esters [2]. The initial difficulties in the ...

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23.7 ALKYLATION AND ACYLATION REACTIONS OF AMINES

23.7 ALKYLATION AND ACYLATION REACTIONS OF AMINES

This provides a way to introduce methyl groups to the level of a tertiary amine: (Quaternization does not occur in these reactions. Why?) Neither an imine nor an enamine can be an intermediate in the reaction of a secondary amine with formaldehyde (Eq. 23.27). (Why?) In this case a small amount of a cationic intermediate, an imminium ion, is formed in solution by protonation of a carbinolamine ...

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J. Org. Chem. 1984,49, 2081-2082 208 1

J. Org. Chem. 1984,49, 2081-2082 208 1

N-Dealkylation of Tertiary Amines: Improved Syntheses of Naltrexone and Nalbuphine Summary: ... dealkylation with BrCN, only ring scission products are obtained from both reactants.6 However, as predicted benzyl cleavage is preferred over methyl loss: with ACE-C1, glaucine (5) affords the ring-opened phenanthrene 6 (89% yield). Even dealkylation of aromatic amines occurs (1) With complex ...

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4-Chlorophenyl and 2,4,6-tribromophenyl ...

4-Chlorophenyl and 2,4,6-tribromophenyl ...

The accepted pathway9 for dealkylation of tertiary amines with chloroformates involves the rate determining decomposition of the salt (3) by chloride, forming the carbamate (4) and an alkyl chloride. In a general way this appears also to be the case with chlorothiono-formates.The reaction of unhindered tertiary amine with 4-chlorophenyl chlorothionoformates was very rapid at 20°C in ...

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STUDIES ON THE MECHANISM OF AROMATIC ALKY NATIONS PHENOLS ...

STUDIES ON THE MECHANISM OF AROMATIC ALKY NATIONS PHENOLS ...

2,6-DI- TERTIARY-BUTYLPHENOL PART B: KINETIC STUDIES OF THE ALKYLATION OF PHENOLS WITH TERTIARY HALIDES PART C: THE MECHANISM OF THE INHIBITION OF PHENOL ALKYLATIONS BY OXYGENATED COMPOUNDS Submitted to the School of Graduate Studies of Michigan State College of Agriculture and Applied Science in partial fulfillment of the requirements for the degree of By Frank A. Cassis, Jr. AN ABSTRACT ...

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Discovery, Scope, and Limitations of an N â Dealkylation ...

Discovery, Scope, and Limitations of an N â Dealkylation ...

comprised a dealkylation event followed by Chan Lam aryla-tion of the resulting primary sulfonamide 4 to give 3 b (Pathway A) or Chan Lam arylation of 1 b to deliver tertiary sulfonamide 5 followed by dealkylation to give 3 b (Pathway B). Firstly, benzaldehyde was readily detected as a reaction byproduct,

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An efficient and operationally convenient general ...

An efficient and operationally convenient general ...

Tertiary amines synthesized via direct N-alkylation of secondary amines with alkyl halides in the presence of Hunig’s base a Entry Alkyl Halide Amine Product Amine Yieldsb (%) Timec 1 Ph Br (n-Butyl) 2NH (n-Butyl) 2N Ph > 90 3 hrs 2 Ph Br N H N Ph 91 2 hrs 3 Ph Br N H O N O Ph > 90 2 hrs 4 Ph Br NH Ph N Ph Ph > 90 3 hrs 5 Br HN Ph Ph N Ph Ph > 90 3 hrs 6 Br (n-Hexyl) 2NH (n-Hexyl) 2N > 90 24 ...

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A comparison of several modern alkylating agents

A comparison of several modern alkylating agents

Special Issue Reviews and Accounts ARKIVOC 2009 (i) 251-264 ISSN 1551-7012 Page 252 ©ARKAT USA, Inc. 4.8 Alkoxy-λ6-sulfanenitriles (thiazynes) 4.9 S-Propargyl xanthates 5. Conclusions 1. Introduction The alkylation of various acidic functional groups (Scheme 1) is important in total synthesis, to

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NPC Natural Product Communications

NPC Natural Product Communications

N-dealkylation. For example, the oxidative action of cytochrome P450 enzymes provides an efficient and highly selective means of N-demethylation during metabolic events. However, in the laboratory environment the challenge remains for the organic chemist to provide an efficient, high yielding method of N-demethylating tertiary amines that is chemoselective and proceeds under mild conditions ...

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