78845-08-6

Upstream product

• 27200-84-6 methyl triphenylphosphonium bromide 
• 81925-25-9 2-(E)-(1-buta-1,3-dienyl)-1-(E)-(3-prop-2-en-1-al)cyclohexanol 
• 444346-17-2 (E)-butadienyl-lithium 
• 78845-10-0 2-(E)-(1-buta-1,3-dienyl)cyclohexanone 
• 78845-12-2 (E)-1-tri-n-butylstannyl-1,3-butadiene 
• 81925-24-8 2-trans-(E)-(1-buta-1,3-dienyl)cyclohexanol 
• 81925-32-8 1-(1-buta-1,3-dienyl)-2-chlorocyclohexanol 
• 81925-23-7 1-acetoxy-trans-2-(E)-(1-buta-1,3-dienyl)cyclohexane 
• 822-87-7 2-Chlorocyclohexanone 
• 286-20-4 cyclohexane-1,2-epoxide 
• 78845-11-1 1-(1,3-bis(methylthio)prop-2-enyl)-2-(1-buta-1,3-dienyl)cyclohexanol 
• 19493-09-5 Methylenetriphenylphosphorane 
• 31849-91-9 trans-3-(trans-2-acetoxycyclohexyl)-2-propenal 

Downstream Products

• 78845-09-7 cyclotetradeca-3,5,7-trien-1-one 

Relevant academic research and scientific papers

MACROEXPANSION METHODOLOGY: AN EFFICIENT EIGHT UNIT RING EXPANSION

An efficient eight unit expansion method which is postulated to proceed by either a or consecutive sigmatropic shifts is described.

MACROEXPANSION METHODOLOGY; MEDIUM RING SYNTHESIS BASED ON AN EIGHT UNIT RING EXPANSION PROCESS

Treatment of 1,2-(E,E)-di(1-buta-1,3-dienyl)cyclohexanol (21) with potassium hydride in tetrahydrofuran at room temperature resulted in the facile formation of a 14-membered ring dienolate which on kinetic protonation provided cyclotetradeca-3,5,7-trien-1-one.This novel rearrangement which provides the basis for an efficient, eight unit ring expansion method was also observed when 5,8-dimethyl-5-hydroxy-1,3,7,9-decapentaene (28), the acyclic analogue of 21, was treatad with potassium hydride in tetrahydrofuran.Methodology for the preparation of 21 and 28 including the preparation of 1-lithio-1,3-butadiene is also described.