Practical Multigram Syntheses of Benzocyclobutenediones

Article abstract of DOI:10.1021/jo00141a002

Experimentally simple syntheses of benzocyclobutenedione and substituted benzocyclobutenediones (3-OH; 4-OH; 4-Me; 3-OH, 5-Me) are described which allow the synthesis of these compounds on large scale from inexpensive starting materials.The regiospecific and stereoselective cycloaddition of trimethylsiloxy dienes to 1,4-dichloro-3,3,4-trifluorocyclobutene forms the basis of the synthesis of the substituted benzocyclobutenediones.