20536-36-1

Upstream product

• 503-60-6 3,3-dimethyl-allyl chloride 
• 78-79-5 isoprene 
• 106-25-2 Nerol 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 

Downstream Products

• 70143-03-2 Z-(3,7-dimethylocta-2,6-dienyl)diphenylphosphine oxide 
• 502-61-4 (E,Z)-α-farnesene 
• 106625-35-8 (Z)-2-(3,4-Dimethoxy-phenyl)-5,9-dimethyl-deca-4,8-dienenitrile 
• 56881-52-8 (Z)-(3,7-dimethylocta-2,6-diene-1-sulfonyl)benzene 
• 21488-83-5 (2Z)-1-Phenyl-3,7-dimethyl-2,6-octadiene 
• 82112-41-2 2-[(Z)-4,8-Dimethyl-1-(toluene-4-sulfonyl)-nona-3,7-dienyl]-thiophene 
• 763-10-0 neryl diphosphate 
• 61585-35-1 p-menth-1-ene 
• 2436-90-0 dihydromyrcene 
• 2492-22-0 2,6-dimethylocta-2(Z),6-diene 
• 2609-23-6 (E)-3,7-dimethyl-2,6-octadien 
• 106-25-2 Nerol 
• 137256-10-1 1-<(Z)-3,7-dimethyl-2,6-octadienyl>cyclohexan-1-ol 
• 22555-67-5 cis-9-Phenyl-2,6-dimethyl-nonadien-(2,6) 

Relevant academic research and scientific papers

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers

A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.

Allylic and allenic halide synthesis via NbCl5- and NbBr 5-mediated alkoxide rearrangements

(Chemical Equation Presented) Addition of NbCl5 or NbBr 5 to a series of magnesium, lithium, or potassium allylic or propargylic alkoxides directly provides allylic or allenic halides. Halogenation formally occurs through a metallahalo-[3,3] rearrangement, although concerted, ionic, and direct displacement mechanisms appear to operate competitively. Transposition of the olefin is equally effective for allylic alkoxides prepared by nucleophilic addition, deprotonation, or reduction. Experimentally, the niobium pentahalide halogenations are rapid, afford essentially pure (E)-allylic or -allenic halides after extraction, and are applicable to a range of aliphatic and aromatic alcohols, aldehydes, and ketones. 2009 American Chemical Society.

Semiempirical AM1 Calculations on the Competing 1- and 4-Alkylation of 2-Methylbuta-1,3-diene with Primary Allylic Cations

The strict regioselectivity of the attack of various carbenium ions on 2-methylbuta-1,3-diene at C-1 is not valid in the case of primary-tertiary allylic cations (such as 2-5) which also attack at C-4 (≈20%), a phenomenon which is rationalized by a cyclic HOMO-LUMO interaction of isoprene and allylic cations.