Example:

T. Hudlicky, J. P. Sheth, Tetrahedron Lett. 1979 , 29 , 2667.

J. M. Jimenez, R. M. Ortuno, Tetrahedron: Asymmetry 1996 , 7 , 3203.

 

5.3.3 Addition Reactions

The 1,3-dipolar addition of reaction of diazomethane with a variety of compounds having ethylenic and acetylenic bonds afford heterocyclic compounds (Scheme 11).

Scheme 11

5.3.4 Cycloaddition

Heat as well as light produces carbene from diazomethane through loss of nitrogen that can add to alkenes to give cyclopropane derivatives (Scheme 12). If the reaction is diluted with a large amount of an inert solvent, the carbene undergoes more collisions before it reacts and so the chances of flipping singlet to triplet carbene are increased. Addition to alkenes is then less stereospecific.

Scheme 12

Text Book

M. B. Smith, Organic Synthesis , 2 nd Ed., McGraw Hill, Singapore, 2004.