17475-41-1

Upstream product

• 136391-65-6 diazomethane 
• 557-20-0 diethylzinc 
• 91587-24-5 diazomethane 

Downstream Products

• 90843-22-4 2-(prop-1-en-1-yl)benzoic acid 
• 2438-03-1 2-(n-Propyl)-benzoesaeure 
• 58931-27-4 1-(1-hydroxypropyl)-2-hydroxymethylbenzene 
• 952412-85-0 C₁₀H₁₂O₃ 
• 99291-13-1 α-ethyl-α,α'-dibromoxylene 
• 97567-64-1 2-n-Propylbenzonitrile 

Relevant academic research and scientific papers

Solid-phase synthesis of isoindolinones and naturally-occurring benzobutyrolactones (phthalides) using a cyclative-cleavage approach

Starting from Merrifield resin, 2-formylbenzoic acids were immobilized on solid supports. Reactions between immobilized 2-formylbenzoic acids and different organometallic reagents (Grignard reagents, zinc reagents, allyl silanes via Sakurai type reactions) furnished secondary alcohols which cyclized depending on the metal counter ion and reaction conditions, forming benzoannelated lactones. Asymmetric synthesis was possible on the resin using chiral [2.2]paracyclophane ligands. While the reaction of immobilized ortho-carboxy benzaldehydes with primary amines at elevated temperatures yielded 3-hydroxyisoindolinones, a reaction at ambient temperature allowed imine formation, which underwent 1,2-addition-cleavage reaction with various nucleophiles, yielding isoindolinones with three points of diversity.

Intervention of carbonyl and oxonium ylides in reactions of [(alkoxycarbonyl)phenyl]carbenes in the gas phase forming 3-alkylphthalides and 2-alkoxy-1(2H)-benzocyclobutenone. 13C and 18O labeling studies

The generation of isomeric [(methoxycarbonyl)phenyl]carbenes (6a-c) by flash vacuum pyrolysis (FVP, 350-450 C, 10-5 Torr) of the corresponding diazomethanes (1a-c) produced 3-methylphthalide (2) and 2-methoxy-l(2H)-benzocyclobutenone (3), presumably as a result of carbene-carbene rearrangement followed by the interaction of the methoxycarbonyl group with the carbene center in the ortho isomer (6a). Labeling studies were carried out in order to determine the mechanism of the reaction. Thus, FVP of [o-(carboxy-13C](methoxycarbonyl)phenyl]diazomethane produced 3-methyl[carbonyl-13C]phthalide and 2-methoxy-1(2H)-[carbonyl-13C]benzocyclobutenone, thereby indicating that 3 was formed via Stevens-type migration of the acyl group in an oxonium ylide intermediate (9). FVP of [p-[carfronyl-18O](methoxycarbonyl)phenyl]diazomethane, on the other hand, produced 3-methyl[ether-18O]phthalide, along with a small amount of 3-methyl[carbonyl-18O]phthalide and 3-methoxy-1(2W)-[carbonyl-18O]benzocyclobutenone, indicating that 2 was produced mainly via 1,5-methyl migration in a carbonyl ylide intermediate (7). Generation of other [(alkoxycarbonyl)phenyl]diazomethanes (16, where alkoxy = EtO and PriO) under similar conditions also produced 3-alkylphthalides (17) and 2-alkoxybenzocyclobutenones (18), but phthalide 19, which was not detected in the FVP of 1, was also formed in this case, presumably as a result of α,β-elimination of alkenes in the oxonium ylide. These results showing the intervention of the oxonium ylide of the ester group are in marked contrast to the observation that, at much lower temperatures in the liquid and solid phases, only the carbonyl ylide has been involved.