874964-01-9

Upstream product

• 4045-44-7 1,2,3,4,5-pentamethylcyclopentadiene 
• 2043-61-0 cyclohexanecarbaldehyde 
• 874963-98-1 1-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-1-dodecanol 
• 874964-03-1 10-chloro-1-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-1-decanol 
• 874964-02-0 7-hydroxy-7-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)heptanenitrile 
• 874964-04-2 methyl 6-hydroxy-6-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)hexanoate 
• 874964-00-8 1-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-3-phenyl-1-propanol 

Downstream Products

• 862387-15-3 {4-[(hydroxy)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methyl]phenyl}(phenyl)methanone 
• 4045-44-7 1,2,3,4,5-pentamethylcyclopentadiene 
• 2043-61-0 cyclohexanecarbaldehyde 
• 63126-49-8 (+/-)-1-cyclohexyl-1-pentanol 

Relevant academic research and scientific papers

Chlorodimethylaluminum-promoted nucleophilic addition of lithium pentamethylcyclopentadienide to aliphatic aldehydes and DDQ-mediated carbon-carbon bond cleavage of the adducts providing the parent aldehydes

Treatment of aliphatic aldehyde with lithium pentamethylcyclopentadienide in the presence of chlorodimethylaluminum provided the corresponding carbinol in excellent yield. The carbinol returns to the parent aldehyde and pentamethylcyclopentadiene by the a

Pentamethylcyclopentadienide in organic synthesis: Nucleophilic addition of lithium pentamethylcyclopentadienide to carbonyl compounds and carbon-carbon bond cleavage of the adducts yielding the parent carbonyl compounds

Lithium pentamethylcyclopentadienide (C5Me5Li, Cp*Li) reacted with aromatic aldehyde to provide the corresponding carbinol in excellent yield. The carbinol returns to the parent aldehyde and pentamethylcyclopentadiene upon exposure to acid or due to heating. Chlorodimethylaluminum is essential as an additive to attain the nucleophilic addition of Cp*Li to aliphatic aldehyde. The carbinol derived from aliphatic aldehyde returns to the parent aldehyde and pentamethylcyclopentadiene by the action of a catalytic amount of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ). The reversible addition/elimination of the Cp* group can represent a protection of aldehyde. Mechanistic details of the carbon-carbon bond cleavage are also disclosed.