133213-19-1

Basic information

• Product Name: 5-Isopropyl-2-methyl-cyclohexa-2,5-dienyl-hydroperoxide
• Synonyms: 5-Isopropyl-2-methyl-cyclohexa-2,5-dienyl-hydroperoxide
• CAS NO: 133213-19-1
• Molecular Weight: 168.236
• Mol File: 133213-19-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 5-Isopropyl-2-methyl-cyclohexa-2,5-dienyl-hydroperoxide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Isopropyl-2-methyl-cyclohexa-2,5-dienyl-hydroperoxide(133213-19-1)
• EPA Substance Registry System: 5-Isopropyl-2-methyl-cyclohexa-2,5-dienyl-hydroperoxide(133213-19-1)

Safety Data

• Hazardous Substances Data: 133213-19-1(Hazardous Substances Data)

Upstream product

• 4221-98-1 (R)-5-isopropyl-2-methylcyclohexa-1,3-diene 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 

Relevant articles and documents

Competition of Endoperoxide and Hydroperoxide Formation in the Reaction of Singlet Oxygen with Cyclic, Conjugated Dienes

Rose-bengal-sensitized photooxygenation of (-)-(R)-α-phellandrene (1) in MeOH at room temperature yielded a complex mixture of products, contrary to previous reports describing cis-(3S,6R)-epidioxy-p-menthene (2) and trans-(3R,6S)-epidioxy-p-menthene (3) as the only products.The mixture was separated by prep.HPLC (silica gel, pentane/Et2O 9:1).Besides the known endoperoxides 2 (yield 39 percent) and 3 (26 percent), all those hydroperoxides, which can be deduced from an ene reaction of 1O2 with 1, were isolated, i. e. 4β-p-mentha-2,5-dien-1β-yl hydroperoxide (4) (14 percent), 4β-p-mentha-2,5-dien-1α-yl hydroperoxide (5) (9 percent), (2R,4R)-p-mentha-1(7),5-dien-2-yl hydroperoxide (6) (2.1 percent), (2S,4R)-p-mentha-1(7),5-dien-2-yl hydroperoxide (7) (1.5 percent) and (1R)-p-mentha-3,6-dien-yl hydroperoxide (8; 1.5 percent; Scheme 1).Furthermore, the constant cis/trans ratio for all diastereoisomeric pairs (2/3, 4/5, 6/7) was striking.With the help of the two possible conformers 1a and 1b of the starting material a model of a common first step for endoperoxide as well as for hydroperoxide formation is developed.A photooxygenation at -50 deg C supports this model.The absolute value of the cis/trans ratio changes in the same way for the endoperoxides and the hydroperoxides.