Synthesis of spiro[4.5]trienones by intramolecular ipso-halocyclization of 4-(p-methoxyaryl)-1-alkynes.
A wide variety of 3-halospiro[4.5]trienones are readily prepared in good to excellent yields by the intramolecular ipso-halocyclization of 4-(p-methoxyaryl)-1-alkynes under mild reaction conditions. ICl, I2, and Br2 are all effective electrophiles for this process under carefully optimized reaction conditions.
Zhang
Xiaoxia
X
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Larock
Richard C
RC
D000480:Alkynes / Q000737:chemistry*; D000840:Anisoles / Q000737:chemistry*; D003500:Cyclization; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis*
D000480:Alkynes; D000840:Anisoles; D006846:Hydrocarbons, Halogenated; D013141:Spiro Compounds; C060998:anisole