86459-90-7

Upstream product

• 1569-50-2 3-penten-2-ol 
• 127492-03-9 1-(phenylsulfinyl)-2,2,2-triethoxyethane 

Downstream Products

• 41033-79-8 1,3,3-Trimethyl-2-((1E,3Z)-3-methyl-penta-1,3-dienyl)-cyclohexene 
• 51468-89-4 1,3,3-trimethyl-2-[(1E,3E)-3-methyl-1,3-pentadienyl]cyclohexene 
• 3899-20-5 ethyl (all-E)-retinoate 
• 1185252-37-2 C₁₄H₂₀O₂ 
• 96177-47-8 3,7,11-trimethyl-13t-(2,6,6-trimethyl-cyclohex-1-enyl)-trideca-2t,4t,6t,8t,10t,12-hexaenoic acid ethyl ester 

Relevant academic research and scientific papers

One-Flask, Regiospecific Conversions of Allylic Alcohols into Two-Carbon-Extended, Conjugated Dienoate Esters. Use of a New Sulfinyl Orthoester

Sixteen differently substituted primary and secondary allylic alcohols are shown to react with sulfinyl orthoacetate 1 at 100 deg C sequentially via a sigmatropic rearrangement and then a β-elimination of benzenesulfenic acid to form conjugated dienoate esters 5-13 in 45-95percent yields.This one-flask, intramolecular carbon-carbon bond-forming process represents a simple and convenient method for regiospecific γ-attachment of a two-carbon (ethoxycarbonyl)methylene unit via the synthetic equivalent of an SN2' process.Two examples are given in which rationally designed dienoates 20 and 24, prepared via this one-flask process and carrying a pendant alkene unit, undergo intramolecular 2+4 cycloaddition producing bicyclic cyclohexenes 21 and 25.