Page 891 - Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey _ Sundberg

Scheme 10.6. 1,3-Dipolar Cycloadditions 875

1,3-Dipole Alkenyl Alkynyl SECTION 10.3
dipolarophile dipolarophile 1,3-Dipolar
Cycloaddition Reactions
N N
– + N R N R
RN N N + RCH CHR N N
azide R R
R R
1,2,3-triazoline 1,2,3-triazole
N R N R
N N
– +
C N N R R
R 2 + RCH CHR R R
R R
diazoalkane
1-pyrazoline 3H-pyrazole
R R
– + N R N R
R C N CR + RCH CHR R R
2
nitirile ylide R R
R R
1-pyrroline 2H-pyrrole
R R
– + N R N R
RN N CR + RCH CHR N N
nitrile imine R R
R R
2-pyrazoline pyrazole
R R
– + R
O N CR + RCH CHR N R N
nitrile oxide O O
R R
2-isoxazoline isoxazole
R R
R R R R
– + N R N R
R C N CR 2 + RCH CHR R R
2
R R
R R R
azomethine ylide pyrrolidine 3-pyrroline
R R
R R
R R
– + R N R N
RN N CR 2 + RCH CHR N N
R R
R R R
azomethine imine pyrazolidine 3-pyrazoline
R R
R R
– + R R
O N CR2 + RCH CHR R N R N
O O
R R R
nitrone isoxazolidine 4-isoxazoline