66557-15-1

Upstream product

• 526-86-3 2,3-dimethyl-1,4-benzoquinone 
• 24850-33-7 allyltributylstanane 
• 762-72-1 allyl-trimethyl-silane 
• 3732-03-4 4-hydroxy-2,3-dimethylphenyl allyl ether 
• 608-43-5 2,3-dimethyl-1,4-dihydroxybenzene 

Downstream Products

• 607351-67-7 5-hydroxy-2,6,7-trimethyl-2,3-dihydrobenzofuran-4-carbaldehyde 
• 3731-98-4 5-Allyl-2,3-dimethyl-benzochinon 

Relevant academic research and scientific papers

Bi(OTf)3-catalyzed allylation of quinones with allyltrimethylsilane

p-Quinones react smoothly with allyltrimethylsilane in the presence of 2 mol% of Bi(OTf)3 under mild reaction conditions to afford the corresponding allyl substituted benzene derivatives, p-allylquinols and allyl substituted 1,4-naphthoquinones in excellent yields with high regioselectivity. This method is very useful for the direct introduction of an allyl functionality onto a quinone moiety.

Development of novel antioxidants: Design, synthesis, and reactivity

We are attempting to develop novel synthetic antioxidants aimed at retarding the effects of free-radical induced cell damage. In this paper we discuss the design strategy and report the synthesis of seven novel antioxidants, including six catechols and a

Allylation of Quinones with Allyltin Reagents

Lewis acid (BF3) catalyzed allylation of quinones with allyl- (2a), 2-methyl-2-propenyl- (2b), trans-2-butenyl- (2c,d), 3-methyl-2-butenyl- (2e,f), and trans-cinnamyltrialkyltin (2g) gives the corresponding allylhydroquinones with high regioselectivity.Vitamin K2(5) (7) and coenzyme Q1 (9) were prepared in yields of 78 and 75percent, respectively.These reactions appear to proceed through allylquinol intermediates which undergo rearrangement under the influence of BF3.The success of this synthesis of vitamin K2(5) and coenzyme Q1 depends on the fact that the reaction of 3-methyl-2-butenyltin with quinones occurs at the α carbon of the allylic system.

929. Chrom-3-en-6-ols. The action of pyridine on alk-2-enyl-benzoquinones

Allylbenzoquinones are converted by treatment with pyridine into quinols and chrom-3-en-6-ols. The tendency for the latter reaction to occur increases as the benzoquinone ring becomes more highly substituted.