29800-55-3

Upstream product

• 75-11-6 diiodomethane 
• 62249-35-8 (Z)-2-cycloocten-1-ol 
• 19935-88-7 N,N'-Dinitroso-N,N'-diaethoxycarbonyl-1,3-propandiamin 
• 108-94-1 cyclohexanone 
• 286-60-2 bicyclo[6.1.0]nonane 
• 122950-18-9 (1R^*,8S^*)-bicyclo<6.1.0.>nonan-2-one 1,4-di-O-benzyl-L-threitol ketal 
• 1728-25-2 2-cycloocten-1-one 
• 3212-75-7 2-cycloocten-1-ol 
• 29783-12-8 anti-(1α,2α,8α)-Bicyclo<6.1.0>nonan-2-ol 

Downstream Products

• 122950-18-9 C₂₇H₃₄O₄ 

Relevant academic research and scientific papers

A NEW METHOD FOR DIRECT OXIDATION OF THE METHYLENE GROUP ADJACENT TO A CYCLOPROPANE RING TO THE KETO GROUP

A new finding that the methylene group adjacent to a cyclopropane ring can be oxidized to the keto group directly with ruthenium tetroxide is described.

Direct Oxidation of Cyclopropanated Cyclooctanes as a Synthetic Approach to Polycyclic Cyclopropyl Ketones

A series of polycyclic hydrocarbons containing cyclopropane moieties 1,2-annelated or spiro-condensed with a cyclooctane ring were investigated under oxidative conditions. Four oxidizing systems (O3 on SiO2, a dioxirane derived from trifluoroacetone, CrO3, and RuO4, generated in situ), were tested to evaluate and compare their reactivity and usefulness. RuO4 was found to be the best of them, considering its oxidative power together with the simple operating procedure. Conditions for the specific oxidation of polycyclic hydrocarbons were found. New cyclooctane derivatives containing cyclopropyl carbonyl moieties were obtained.

Another Role of Copper in the SimmonsSmith Reaction: Copper-catalyzed Nucleophilic Michael-type Cyclopropanation of a,β-Unsaturated Ketones

Cyclopropanation was performed using the Furukawa procedure with CH2I2/Et2Zn and a,β-unsaturated ketones. The reaction was performed in the presence of a copper salt. The reactivity was highly dependent on the substrate structure, and cyclopropanated products were obtained in better yields than those achieved using the original SimmonsSmith conditions with a ZnCu couple in some cases. Stereospecificity was observed in a certain case; however, the synthesis of an asymmetric version with a chiral ligand was not successful.