71104-80-8

Upstream product

• 2622-05-1 allylmagnesium bromide 
• 108-24-7 acetic anhydride 
• 123-11-5 4-methoxy-benzaldehyde 
• 54835-91-5 trans-<2-(p-methoxyphenyl)cyclopropyl>methyl acetate 
• 14202-31-4 4-methoxybenzaldehyde-1,1-diacetate 
• 106-95-6 allyl bromide 
• 24165-60-4 1-(4-methoxyphenyl)but-3-en-1-ol 
• 64-19-7 acetic acid 
• 123-38-6 propionaldehyde 
• 24165-60-4 (S)-1-(4-methoxyphenyl)but-3-en-1-ol 
• 7393-43-3 tetraallyl tin 
• 6142-64-9 (1R*,2R*)-ethyl 2-(4-methoxyphenyl)cyclopropanecarboxylate 
• 762-72-1 allyl-trimethyl-silane 
• 67-56-1 methanol 

Downstream Products

• 106730-47-6 2-[(E)-2-(4-Methoxy-phenyl)-vinyl]-cyclopropanecarboxylic acid ethyl ester 
• 24165-60-4 1-(4-methoxyphenyl)but-3-en-1-ol 
• 1613331-71-7 1-(4-methoxyphenyl)-3-oxobutyl acetate 
• 106730-37-4 (1S,2S)-2-(4-Methoxy-phenyl)-cyclopent-3-enecarboxylic acid methyl ester 
• 106730-37-4 (1R,2S)-2-(4-Methoxy-phenyl)-cyclopent-3-enecarboxylic acid methyl ester 
• 108409-76-3 2-(4-Methoxy-phenyl)-cyclopent-3-enecarboxylic acid methyl ester 
• 106730-43-2 (1S,2S)-2-(4-Methoxy-phenyl)-cyclopent-3-enecarboxylic acid 
• 106730-33-0 2-[(E)-2-(4-Methoxy-phenyl)-vinyl]-cyclopropanecarbonyl chloride 
• 24165-60-4 (+)-1-(4-methoxyphenyl)-3-buten-1-ol 
• 24165-60-4 (-)-1-(4-methoxyphenyl)-3-buten-1-ol 

Relevant academic research and scientific papers

Study on the coupling of acyclic esters with alkenes - The synthesis of 2-(2-hydroxyalkyl)cyclopropanols via cascade cyclization using allylsamarium bromide

The radical cyclization between aliphatic acyclic esters and alkenes was achieved unprecedentedly in the presence of allylsamarium bromide with HMPA and H2O as additives. The cascade radical cyclization-ring-opening- anionic cyclization allowed facile and efficient access to 2-(2-hydroxyalkyl) cyclopropanols from readily available materials.

High Atom Efficiency in Sc(OTf)3-Catalyzed Allylation of Aldehydes with Tetraallyltin

The high atom efficiency was achieved through addition of Ac2O in the Sc(OTf)3-catalyzed allylation of aldehyde with tetraallytin in a 4:1 molar ratio.

Prins cyclizations: labeling studies and application to natural product synthesis.

The first syntheses of two natural products, catechols 1 and 2, isolated from Plectranthus sylvestris (labiatae), are reported. Oxygen-18 labeling studies support the proposed intermediacy of a stabilized benzylic cation in the acid-promoted cyclization of an aldehyde and benzylic homoallylic alcohol possessing an electron-rich aromatic ring. In contrast, with an electron-deficient aromatic ring the pathway via a benzylic cation is only minor. [reaction: see text]

Oxonia-Cope rearrangement and side-chain exchange in the Prins cyclization

(Formula Presented) TMSOAc OAc OAc 2 3 Evidence is presented here for the mechanism of the Prins cyclization of benzylic homoallylic alcohols, which shows that the outcome of the reaction is dependent upon the substituents on the aromatic ring. The presence of an electron-rich aromatic ring favors an oxonia-Cope rearrangement yielding a symmetrical tetrahydropyran as the major product formed via a side-chain exchange process. In contrast, with electron-deficient aromatic rings the expected 2,4,6-trisubstituted tetrahydropyran is formed.

Indium-mediated allylation of gem-diacetates to homoallylic acetates in aqueous media

Indium-mediated allylation of gem-diacetates gave excellent yields of the corresponding homoallylic acetates in aqueous media. (C) 2000 Elsevier Science Ltd.

Sc(OTf)3, an efficient catalyst for addition of allyltrimethysilane to aldehydes: Chemoselective addition to aldehydes in presence of ketone and in situ acylation (3-component coupling)

Scandium triflate (2-10 mol%) have been found to be a highly efficient catalyst for the addition of allyltrimethylsilane to both activated aromatic and aliphatic aldehydes. However, deactivated (electron rich) aromatic aldehydes gave double allylated products instead. Using a stoichiometric amount of Ac2O in the allylation reaction led directly to homoallylic acetates [in situ acylation catalysed by Sc(OTf)3] and for the first time gave high yields of adducts with moderately electron rich aromatic aldehydes.

ARYLCYCLOPROPANE PHOTOCHEMISTRY. UNUSUAL AROMATIC SUBSTITUENT EFFECTS ON THE PHOTOCHEMICAL REARRANGEMENT OF (2-ARYLCYCLOPROPYL)METHYL ACETATES TO 1-ARYLHOMOALLYL ACETATES.

Irradiation of trans(2-arylcyclopropyl)methyl acetates a 4-butenyl-1-arylacetate (7a,b,d-h) via an ionic mechanism from the singlet state. Similar rearrangements occurred with exo-(1,1a,6,6a-tetrahydrocycloprop left bracket a right bracket inden-1-yl)methyl acetate and the 4-cyano derivative. Excited state reaction rate constants were determined from reactant fluorescence lifetimes and product quantum yields. It is concluded that the rate-determining step involves conversion of the initially formed aromatic excited state to a reactive cyclopropane excited state and that cyclopropane to aromatic ring charge transfer enhances this process.

LEWIS ACID CATALYZED REARRANGEMENT OF VINYLCYCLOPROPANECARBONYL CHLORIDE TO CYCLOPENTENECARBONYL CHLORIDE

Vinylcyclopropane-cyclopentene rearrangement of 2-(2-aryl-vinyl) cyclopropanecarbonyl chlorides was observed upon treatment with a Lewis acid under mild reaction conditions to afford 2-arylcyclopent-3-enecarboxylates after esterification.