73741-72-7

Upstream product

• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 75265-49-5 3-deuteriocyclohex-2-en-1-one 
• 80642-13-3 C₁₃H₁₁⁽²⁾HN₂O₆ 
• 55282-88-7 1-deuteriocyclohex-2-en-1-ol 

Downstream Products

• 55282-88-7 1-deuteriocyclohex-2-en-1-ol 
• 102853-28-1 γ-deuterio-2-cyclohexenyl pivalate 
• 114538-21-5 3-d1-2-Cyclohexen-1-ylacetat 

Relevant academic research and scientific papers

On the Solvolysis of 2-Cyclohexenyl 3,5-Dinitronbenzoate and p-Nitrobenzoate in Aqueous Acetone. Introduction of Acyl-Oxygen Cleavage by Basic Buffer Systems

Solvolysis of α- and β-deuterium-labeled 2-cyclohexenyl 3,5-dinitrobenzoate (1-ODNB) and p-nitrobenzoate (1-OPNB) in 60percent aqueous acetone containing diisopropylethylamine (to protect initially formed product from subsequent acid-catalyzed allylic rea

Mitsunobu Reaction of Unbiased Cyclic Allylic Alcohols

The stereochemical inversion of unbiased allylic alcohols using triphenylphosphine, diethyl azodicarboxylate, and benzoic acid, commonly known as the Mitsunobu reaction, was studied in three different solvents with specific attention toward the product composition. The results generated for the Mitsunobu reaction of (R)-3-deuterio-2-cyclohexen-1-ol and the cis and trans isomers of 1-deuterio-5-methyl-2-cyclohexen-1-ol, 1-deuterio-5-tert-butyl-2-cyclohexen-1-ol, and optically active cis and trans 5-isopropyl-2-methyl-2-cyclohexen-1-ol all gave similar product distributions with respect to inversion and retention at the carbinol center as well-as syn and anti Sn2′ type addition when THF or benzene was used as the solvent (CH2Cl2 gave less selective product distributions). Interestingly, it was found that the quasi-equatorial and quasi-axial nature of the starting allylic alcohol does not appear to affect the product distribution for this reaction, nor does methyl substitution at the central carbon of the allylic alcohol. In all cases, significant amounts (8-28%) of non-SN2 type products were detected for these sterically unbiased allylic alcohols; only 72-77% of the product was from SN2 type reaction when sterically undemanding (R)-S-deuterio-2-cyclohexen-1-ol was subjected to Mitsunobu conditions.

ISOMERIZATION OF PRIMARY ALLYLIC ALCOHOLS TO TERTIARY ONES BY MEANS OF Me3SiOOSiMe3-VO(acac)2 CATALYST

The title rearrangement proceeds in dichloromethane at 25 oC in the presence of the catalyst prepared in situ to give tertiary isomers in good yields.Other rearrangements of sec. -> tert. or sec. -> sec. have been examined.