83303-57-5

Upstream product

• 14578-68-8 4-phenyl-3,4-dihydronaphthalen-1(2H)-one 
• 14578-67-7 4,4-diphenylbutanoic acid 

Downstream Products

• 90036-51-4 (1aS,3R,7bR)-1,3-Diphenyl-1,2,3,7b-tetrahydro-1-aza-cyclopropa[a]naphthalene-1a-carboxylic acid methyl ester 
• 54988-93-1 methyl 4-phenyl-2-naphthoate 
• 90625-85-7 (3S,3aS,5S,9bS)-2,3,5-Triphenyl-2,3,5,9b-tetrahydro-4H-benzo[e]isoindole-1,1,3a-tricarboxylic acid trimethyl ester 
• 118304-02-2 (3aS,5R,9bS)-5-Phenyl-1,4,5,9b-tetrahydro-benzo[e]indazole-3a-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Calcium-catalyzed, dehydrative, ring-opening cyclizations of cyclopropyl carbinols derived from donor-acceptor cyclopropanes

A calcium-catalyzed, dehydrative, ring-opening cyclization of (hetero)aryl cyclopropyl carbinols is reported. The cyclopropyl carbinols are prepared directly from the corresponding donor-acceptor (D-A) cyclopropanes. The calcium catalyst catalyzes the formation of putative (hetero)aryl cyclopropyl carbinyl cations that undergo ring-opening to allylcarbinyl cations. Subsequent intramolecular Friedel-Crafts reaction affords (hetero)aryl-fused cyclohexa-1,3-dienes in up to 97% yield. This approach represents the first example of catalysis for this intramolecular, dehydrative ring-opening cyclization and outperforms the previous reports using stoichiometric Lewis acids.

2,3-Dichloro-5,6-dicyano-para-benzoquinone (DDQ)/methanesulfonic acid (MsOH)-mediated intramolecular arene-alkene oxidative coupling

An efficient intramolecular arene-alkene oxidative coupling of 1,4-diaryl-1,3-butadienes has been developed involving the use of a 2,3-dichloro-5,6-dicyano-para-benzoquinone (DDQ)/acid catalyst. The reaction involves the generation of a radical cation by abstraction of an electron from the substrate with DDQ, an intramolecular Friedel-Crafts-type reaction, and the loss of hydrogen radical.

Lewis acid-mediated highly regioselective ring-expansion of methyl 2-phenyl-1-(arylhydroxymethyl)cyclopropanecarboxylates

A novel ring-expansion of methyl (arylhydroxymethyl)- cyclopropanecarboxylates 1 using Sc(OTf)3 or BF3· OEt2 afforded 1,2-dihydronaphthalene-3-carboxylic acid ester 2 in high to excellent yields. In the reaction, highly regioselective ring opening of cyclopropane and sequential cyclization occurred.

Synthese de methoxycarbonylindenes, dihydro-1,2 naphtalenes et benzocycloheptene. Obtention des indanones-1, des tetralones-1 et de la benzosuberone correspondantes

The synthesis of methoxycarbonylindenes, 1,2-dihydro-naphtalenes, and benzocycloheptene starting from the corresponding 1-indanones, 1-tetralones, and benzosuberone is reported.The starting ketones were synthesized by methods described in the literature which were optimized; in some cases new processes are described.