72448-90-9

Upstream product

• 507-19-7 t-butyl bromide 
• 106175-54-6 1-(p-methoxyphenyl)propenyl-lithium 
• 15546-42-6 [1,1'-(butane-1,4-diyl)bis(triphenylphosphonium)] dibromide 
• 123-11-5 4-methoxy-benzaldehyde 
• 53484-50-7 (E)-p-methoxy-cinnamyl alcohol 
• 84092-48-8 1,6-bis-(p-methoxyphenyl)-1,6-hexanediol 
• 94607-41-7 (E)-1-(4-methoxyphenyl)-3-chloropropene 
• 30043-41-5 (hex-5-enyl)magnesium bromide 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 

Relevant academic research and scientific papers

Synthesis of ocimin, a 1,5-diene, by a bis-Grignard reaction

Ocimin, 1,6-bis-(4-methoxyphenyl)-(E)-(E)-hexa-1,5-diene, was synthetized by the bis-Grignard reaction of p-anisaldehyde with 1,4-bis- (bromomagnesium)butane and the dehydration of the intermediate diol using triphenylphosphine-carbon tetrachloride.

Nickel-Catalyzed Homo- And Cross-Coupling of Allyl Alcohols via Allyl Boronates

A nickel-catalyzed homo- and cross-coupling of allylic alcohols to 1,5-dienes in the presence of B2pin2 with excellent regioselectivity has been developed. Mechanistic studies indicate that the reaction proceeds via sequential nickel-catalyzed borylation of allyl alcohols followed by cross-coupling of the resulting allyl boronates with allyl alcohols. The method was effectively applied to nickel-catalyzed allylation of aldehydes using allylic alcohols directly.

Synthesis of neolignan ocimin and analogues by titanium mediated coupling of methoxycinnamyl alcohols

Coupling of Methoxycinnamyl alcohols to form Ocimin, and its 1,6-bis- diaryl-(E)-(E)- hexa-1,5-diene analogues was effected using McMurry reagents TiCl3/Zn-Cu or TiCl3/LiAlH4. Linear and branched products were obtained wit

Reaction of Phenyl-Substituted Allyllithiums with tert-Alkyl Bromides. Remarkable Difference in the Alkylation Regiochemistry between a Polar Process and the One Involving Single-Electron Transfer

The reaction of phenyl-substituted allyllithiums 1a-h with tert-alkyl bromides was investigated systematically.The alkylation regiochemistry was influenced in a complicated fashion by various factors including substituent effects, both steric and electronic, solvents, and the presence of strongly coordinating additives, tetramethylethylenediamine and hexamethylphosphoramide.On the basis of the cyclizable probe experiments, the observed regiochemistry was interpreted as follows. (a) The reaction proceeds by two alternative pathways, a polar one and single electron transfer (SET), the extent of each path being influenced by the variable factors and (b) a polar pathway favors coupling at the phenyl-substituted site (C-1), while in the case of SET the C-C bond formation occurs predominantly at the site far from the phenyl substituent (C-3).

Reaction of 1-Aryl-3-chloropropenes with Grignard Reagents. Nucleophilic Substitution versus Single-electron Transfer

The reactions of ambident 1-aryl-3-chloropropenes (1a-e) with a series of Grignard reagents, R'MgY (R' = Me, Pr, Ph, Pri, But; Y = Br, I), were carried out in diethyl ether (EE) and tetrahydrofuran (THF).The products were a mixture of two alkylation products (2) and (3), and three dimerization products (4)-(6).The alkylation:dimerization ratio and the composition of the two alkylation products were a marked function of substituent electronic effects in the chlorides (1a-e), R' or Y of R'MgY, and solvent.On the basis of the stereochemistry of alkylation, cyclizable probe experiments, and the effect of the addition of FeCl3 on product composition, the following conclusions were obtained.First, dimers (4)-(6) are most likely to be produced by a mechanism involving single-electron transfer (SET).Second, for the formation of alkylation products (2) and (3), three alternative pathways contribute depending on the nature of R'MgY and solvent, (a) competitive SN2-SN2' pathways in the reaction of R'MgBr in EE, (b) a process involving SET in the reaction with R'MgI in EE, and (c) SN2 pathways in the reaction of R'MgBr in THF.

Reaction of 1-Arylpropenyl-lithium with t-Alkyl Bromides. The Influence of Substituent Electronic Effects and Additives on the Course of the Reaction

The reaction of 1-arylpropenyl-lithium (1a-c) with t-alkyl bromides proceeds by either a nucleophilic substitution or single electron transfer mechanism, the preferred pathway being a function of electronic substituent effects and the absence or presence of tetramethylethylenediamine or hexamethylphosphoramide.