1972
DOI: 10.1016/s0040-4039(01)84269-6
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Adamantylideneadamantane peroxide, a stable 1,2-dioxetane.

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Cited by 124 publications
(45 citation statements)
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“…Decomposition of 1,2-dioxetanes is a highly exothermic process, releasing enough energy to allow the generation of products in electronically excited, emissive states (17,18). Although many 1,2-dioxetanes have vanishingly short lifetimes at room temperature, substituents such as adamantyls have been found to confer remarkable stability (16,19) and have permitted the synthesis of stable 1,2-dioxetanes that can be activated by enzymes (20)(21)(22). AMPPD [abbreviation derived from a nonsystematic name, 3-(2'-spiroadamantane)4methoxy4-(3"-phosphoryloxy)phenyl-1,2-dioxetane, disodium salt] is a stable 1,2-dioxetane with a half-life of 1 year in aqueous solution (23).…”
mentioning
confidence: 99%
“…Decomposition of 1,2-dioxetanes is a highly exothermic process, releasing enough energy to allow the generation of products in electronically excited, emissive states (17,18). Although many 1,2-dioxetanes have vanishingly short lifetimes at room temperature, substituents such as adamantyls have been found to confer remarkable stability (16,19) and have permitted the synthesis of stable 1,2-dioxetanes that can be activated by enzymes (20)(21)(22). AMPPD [abbreviation derived from a nonsystematic name, 3-(2'-spiroadamantane)4methoxy4-(3"-phosphoryloxy)phenyl-1,2-dioxetane, disodium salt] is a stable 1,2-dioxetane with a half-life of 1 year in aqueous solution (23).…”
mentioning
confidence: 99%
“…The strained, central four-membered dioxetane ring is known to decompose at elevated temperatures into two ketones, one of which can take an excited state and relax with the emission of a photon, producing the signature bright blue chemiluminescence. Amongst the 1,2-dioxetane family, the bis(adamantyl) derivative is striking for its stability, with an energy barrier to decomposition of 35 kcal/mol and a half-life at room temperature of around 40 years [26], largely because of the steric lock posed by the two adamantyl groups. In 2012, it was shown that the chemiluminescent cycloreversion of this dioxetane could be activated mechanically, giving mechanoluminescence (Fig.…”
Section: Mechanoluminescencementioning
confidence: 99%
“…[82]. A perepoxide intermediate was reported to be trapped in the epoxide form [83] in the reaction of adamantylideneadamantane with singlet oxygen affording dioxetane derivatives [84]. …”
Section: Quasi-intermediate Perepoxidementioning
confidence: 99%