32744-30-2

Basic information

• Product Name: 2-phenyl-4,5-dihydro-3H-naphtho<1,8-bc>furan
• CAS NO: 32744-30-2
• Molecular Weight: 234.298
• Mol File: 32744-30-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-phenyl-4,5-dihydro-3H-naphtho<1,8-bc>furan(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenyl-4,5-dihydro-3H-naphtho<1,8-bc>furan(32744-30-2)
• EPA Substance Registry System: 2-phenyl-4,5-dihydro-3H-naphtho<1,8-bc>furan(32744-30-2)

Safety Data

• Hazardous Substances Data: 32744-30-2(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 2882-19-1 ethyl 2-phenyl-2-bromoacetate 
• 88058-45-1 8-benzyloxy-1,2,3,4-tetrahydro-1-naphthalenone 
• 7695-47-8 8-hydroxy-1,2,3,4-tetrahydro-1-naphthalenone 

Relevant articles and documents

Photocyclization Reactions. Part 3 [1]. Synthesis of Naphtho[1,8-bc]-furans and Cyclohepta[cd]benzofurans Using Photocyclization of 8-Alkoxy-1,2,3,4-tetrahydro-1-naphthalenones and 4-Alkoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ones

Photocyclization reactions were carried out on 8-alkoxy-1,2,3,4-tetrahydro-1-naphthalenones (six-membered ring ketones) 4a-g and 4-alkoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ones (seven-membered ring ketones) 5a-e in acetonitrile. Irradiation of 4a-f gave rearranged naphthyl alcohols 8a-f as major products. In the case of 4g, 2a,3,4,5-tetrahydronaphtho[1,8-bc]furan-2a-ol 6g was obtained. In contrast, irradiation of 5a-e afforded 2,2a,3,4,5,6-hexahydrocyclohepta[cd]benzofuran-2a-ols 9a-e in good yields. The difference in reactivities between 4a-g and 5a-e is attributed to the conformation of six- and seven-membered rings. Conformational and substituent effects in cyclization step of 1,5-biradicals are discussed along with reaction pathways.

Conformational Effects in Photocyclization of Six and Seven-membered Ring Alkoxyketones

Irradiation of 8-alkoxytetrahydro-1-naphthalenones 5 gave rearranged naphthyl alcohols 11 as major products and in contrast, 4-alkoxytetrahydrobenzocyclohepten-5-ones 6 afforded tetrahydrocycloheptabenzofurans 14 in good yields; the difference in reactivities is attributed to the conformation of six- and seven-membered rings.