66348-47-8

Upstream product

• 123-73-9 trans-Crotonaldehyde 
• 71478-45-0 heptylmanganese chloride 
• 109603-91-0 C₇H₁₅BrMn 
• 127623-85-2 undec-2-yn-4-ol 

Downstream Products

• 103668-33-3 3-hydroxymethylcyclohexene 
• 66348-55-8 (+/-)-(Z)-3-methyl-6-isopropenyl-3,9-decadien-1-ol acetate 
• 14476-37-0 undecan-4-one 
• 67233-97-0 (E)-undec-2-en-4-one 

Relevant academic research and scientific papers

Synthesis of allylic and homoallylic alcohols from unsaturated cyclic ethers using a mild and selective C-O reduction approach

Unsaturated cyclic ethers can be mildly and selectively reduced with catalytic amounts of B(C6F5)3 in the presence of an alkylsilane. The allylic position is preferentially reduced with minimal or no scrambling of olefin geometry. For electronically equivalent substrates, steric factors guide the reducing agent to the least substituted site.

Diastereoselectivity in the [2,3]-sigmatropic rearrangement of substituted allylic N,N-dialkylamidosulfoxylates. X-ray molecular structure of [(1′) S*, (S)S*]-(2′E)-4-[[3′-(4″-bromophenyl)-1′-methyl- 2′-propenyl]sulfinyl]-morpholine

By the reaction with three N,N-dialkylamidosulfenyl chlorides 2 bearing representative sizes for the R groups on the nitrogen atom, several substituted secondary E or Z allylic alcohols (1a-h) have been converted into the corresponding pairs of diastereoisomeric allylic sulfinamides (3+-3′a-v), whose ratios have been determined by 1H NMR spectroscopy. Five cases of entirely diastereoselective [2,3]-sigmatropic rearrangement have been observed. The stereochemistry of one pure diastereoisomer 3′m has been determined by single crystal X-Ray analysis. When treated with 4-morpholinesulfenyl chloride, cyclohex-2-en-1-ol is stereoselectively converted to one diastereoisomer of the sulfinamide 5b which, by unambiguous procedures, led to the sane p.tolylsulfoxide 5a already obtained by treatment of cyclohex-2-en-1-ol with toluene-p-sulfenyl chloride.

ORGANOMANGANESE (II) REAGENTS XVIII: COPPER-CATALYZED 1,4-ADDITION OF ORGANOMANGANESE CHLORIDE COMPOUNDS TO CONJUGATED ETHYLENIC ALDEHYDES.

Organomanganese chlorides react with β-mono or β,β-bisubstituted α,β-ethylenic aldehydes in the presence of a catalytic amount of copper chloride to give good yields of 1,4-addition products in THF at -30 deg C.