2900-11-0

Upstream product

• 75-11-6 diiodomethane 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 

Downstream Products

• 1246655-10-6 C₁₂₆H₁₇₄O₃₆S₃ 
• 1246655-02-6 C₃₉H₅₄O₁₂ 
• 1276046-25-3 ethyl 7-(benzylamino)-2-methylene-7-oxoheptanoate 
• 33229-02-6 2-methyleneheptanedioic acid 
• 1276046-20-8 7-benzyl 1-ethyl 2-methyleneheptanedioate 
• 66088-37-7 ethyl 1-methyl-2-oxocyclohexancarboxylate 

Relevant academic research and scientific papers

The Grob/Eschenmoser fragmentation of cycloalkanones bearing β-electron withdrawing groups: A general strategy to acyclic synthetic intermediates

Introduction of a β-electron withdrawing group to cycloalkanones allows facile C-C bond fragmentation. The reaction has been demonstrated with a large range of ring sizes, bearing various leaving and electron withdrawing groups, and using a variety of nitrogen and oxygen containing nucleophiles (>30 examples). The application of fragmentation products to the preparation of substituted γ-lactones has been demonstrated. Mechanistic studies are reported which are suggestive of a Grob/Eschenmoser type reaction.

Facile Ring Expansions of α-Halomethyl β-Keto Esters Mediated with SmI2

Treatment of α-halomethyl β-keto esters with SmI2 afforded their corresponding one-carbon expanded products with the aids of HMPA or NiI2.