672889-90-6

Upstream product

• 90972-44-4 5-bromo-2,2-dimethyl-3-methylene-norbornane 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 7785-70-8 (+)-α-pinene 
• 108-24-7 acetic anhydride 
• 14575-92-9 2,3-epoxy-cis-pinane 
• 508-32-7 1,7,7-trimethyltricyclo[2.2.1.02,6]heptane 
• 97090-49-8 2,3,3-Trimethyl-2,6-diacetoxybicyclo<2.2.1>heptane 
• 512-58-3 (7,7-dimethyl-2,6-cyclo-norbornan-1-yl)-methanol 
• 54672-39-8 exo-2,2-dimethyl-3-methylenebicyclo<2.2.1>heptan-5-ol 

Relevant academic research and scientific papers

Reactions of epoxides prepared from some monoterpenes with acetic anhydride on aluminosilicate catalysts

Reactions of epoxides prepared from α-, β-pinenes and camphene with acetic anhydride on aluminosilicate catalysts (clay K-10, zeolite β) were investigated affording various products of skeleton rearrangements: mono- and diacetates with five- and six-membered rings, and also with norbornane and pinane cores.

Electrochemical Oxidation of Polycyclic Cyclopropanes and Camphene. Novel Synthesis of exo-5,5-Dimethyl-6-methylenebicycloheptan-2-ol (Nojigiku Alcohol)

Anodic oxidation of tricyclene (1a) in acetic acid containing triethylamine, followed by hydrolysis, provides a facile and efficient synthesis of exo-5,5-dimethyl-6-methylenebicycloheptan-2-ol (2a), named "nojigiku alcohol", which was isolated from the essential oil of chrysanthemum japonese.Furthermore, a method for large-scale production of 2a starting from the readily available impure starting tricyclene (1a) has been developed by appropriate selection of reaction conditions.Similar electrooxidation of the related naturally occurring polycyclic methylcyclopropanes, cyclofenchene (1b) and longicyclene (1c), followed by hydrolysis also brought about stereo- and regioselective cleavage of carbon-carbon bonds of the cyclopropane rings to give the corresponding homoallylic alcohols 2b,c in good yields.

Heterolytic Cleavage of Homoallylic Alcohols: Part III - Synthesis and Reactions of Spiro(bicycloheptane-2,1'-cyclopropane). Derivatives with Electrophiles

Spiro(bicycloheptane-2,1'-cyclopropane) derivatives (6, 7 and 8) have been synthesised by cyclopropanation of suitable camphenes.A by-product formed along with 7 during Simmons-Smith reaction with 6-acetoxycamphene, has been assigned the brendanol structure (22).Treatment of 6, 7 and 8 with mercuric salts causes 1,3-cleavage of cyclopropane rings which in the case of 7 and 8 triggers fragmentation and leads to the formation of diene-aldehyde (20).