Chapter_23_reactions

Chapter_23_reactions - N NO CH 3 NH 2 O N-methylnitrosourea...

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
R X NH 3 R NH 2 R NH R N R N 2 3 4 X (X = Cl, Br, I) R NH 2 O R N OH H R N OH OH alkylation by epoxide ring opening 2 R NH 2 R CN R N CN H alkylation by conjugate addition O RNH 2 NaBH 3 CN AcOH N H R Reductive amination O R 2 NH NaBH(OOCCH 3 ) 3 AcOH N R R Reductive amination O AcOH N R R NaBH(OOCCH 3 ) 3 AcOH N R R Reductive amination R 2 NH O RNH 2 H + catalyst N R EtOH N H R Reductive amination H 2 , Pt R N(CH 3 ) 3 R X Ag 2 O, H 2 O or AgOH, H 2 O R N(CH 3 ) 3 R HO R R N(CH 3 ) 3 Hofmann Elimination NH 2 NaNO 2 HCl or HNO 2 nitrous acid N 2 + Cl Diazotization to form a diazonium salt N 2 + Cl H 2 O OH — N 2 + HCl N 2 + Cl X Sandmeyer Reaction: X = Cl, Br, I, CN) CuX NH O O N O O R—X (X = Br, I, OTs) N—R O O 1. H 3 O + ! RNH 2 2. HO COO COO Gabriel Synthesis of primary amines KH or KOH K + NO 2 Sn/HCl or Fe/HCl or H 2 , Pd/C NH 2 Reduction of NO 2 group to amine R NHR' O 1. LiAlH 4 2. H 3 O + R NHR' Reduction of amides Chapter 23 Reactions
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
R Br R CN R Reduction of nitriles to form primary amines 2. H 2 O NH 2 NaCN 1. LiAlH 4 O H H O RNH 2 O NHR Mannich Reaction N N N CH 3 CH 3 N N N CH 3 CH 3 Formation of azo compounds N CH 3 H HONO N CH 3 NO Formation of nitrosamine
Background image of page 2
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: N NO CH 3 NH 2 O N-methylnitrosourea ether H 2 C N N Generation of diazomethane KOH, H 2 O, 0°C Chapter 23 Reactions -continued R N C O R'OH R N O R' H O Reaction of isocyanate with alcohols to form urethanes R NH 2 O Br 2 , HO — H 2 O, ! R—NH 2 Hofmann Rearrangement R Br R N 3 R NH 2 Reduction of azides to form primary amines NaN 3 H 2 , Pd/C R Cl O 1. NaN 3 , ! 2. H 2 O RNH 2 Curtius Rearrangement to form primary amines R Cl O N 3 — R N O N N .. .. heat R N C O + N 2 Curtius Rearrangement R N C O H 2 O RNH 2 + CO 2 R N C O R'NH 2 R N N R' H O Reaction of isocyanate with amines to form ureas H R NH 2 O R N O Br .. .. heat R N C O + Br — Hofmann Rearrangement OBr...
View Full Document

This note was uploaded on 04/22/2009 for the course CHEM 3570 taught by Professor Ganem, b during the Fall '06 term at Cornell.

Page1 / 2

Chapter_23_reactions - N NO CH 3 NH 2 O N-methylnitrosourea...

This preview shows document pages 1 - 2. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online