99810-94-3

Basic information

• Product Name: isopropylideneadamantane-1',1',1',3',3',3'-d₆
• Synonyms: isopropylideneadamantane-1',1',1',3',3',3'-d₆
• CAS NO: 99810-94-3
• Molecular Weight: 182.254
• Mol File: 99810-94-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: isopropylideneadamantane-1',1',1',3',3',3'-d₆(CAS DataBase Reference)
• NIST Chemistry Reference: isopropylideneadamantane-1',1',1',3',3',3'-d₆(99810-94-3)
• EPA Substance Registry System: isopropylideneadamantane-1',1',1',3',3',3'-d₆(99810-94-3)

Safety Data

• Hazardous Substances Data: 99810-94-3(Hazardous Substances Data)

Upstream product

• 700-58-3 2-Adamantanone 
• 666-52-4 [⁽²⁾H₆]acetone 

Relevant articles and documents

Dioxetane Radical Cations in Solution. An ESR and Cyclic Voltammetry Study

The radical cation formed upon electrochemical oxidation either of adamantylideneadamantane 1 in an O2-saturated solution or of the corresponding dioxetane 2 is shown by ESR spectroscopy to be 2+.This radical cation is relatively long-lived in CH2Cl2:CF3CO2H:(CF3CO)2O solvent mixtures at low temperatures.The resolved hyperfine splittings are 0.325 mT (4H) and 0.075 mT (6H).Using deuterated derivatives, the larger splitting has been assigned to two pairs of γeq-protons and the smaller one to the two remaining pairs of γeq-protons and one pair of β-protons, with each β-proton situated in a different adamantylidine moiety of 2+ (the notation β and γeq refers to the stucture of 1).These data are consistent with a C2 conformation of 2+ which is twisted at the dioxetane ring and does not enantiomerize on the hyperfine time scale at -110 deg C.Dioxetane radical cations 11+ and 13+ generated from isopropylideneadamantane 10 and 3-pentylideneadamantane 12, respectively, have also been studied under similar conditions by ESR spectroscopy.Their hyperfine data give no evidence of twisting at the dioxetane rings and provide a further example for the sensitivity of the long-range splittings to orientation of bonds relative to the spin-bearing orbital.Cyclic voltammograms indicate that the Eo' value for 2 is 0.66 V anodic of 1 at -78 deg C, so that electron transfer from 1 to 2+ is exothermic by 15 kcal/mol.