The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-((1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethanol, is researched, Molecular C11H18O, CAS is 35836-73-8, about The photochemical nucleophile-olefin combination, aromatic substitution (photo-NOCAS) reaction. Part 5: methanol-monoterpenes (α- and β-pinene, tricyclene, and nopol), 1,4-dicyanobenzene, the main research direction is photochem nucleophile terpene olefin combination; aromatic substitution dicyanobenzene benzenedicarbonitrile.Category: chlorides-buliding-blocks.
The reactivity of the radical cations of α- and β-pinene (I and II), tricyclene (III), and nopol (IV) has been studied. The radical ions were generated, in acetonitrile-methanol (3:1), by single electron transfer (set) to the singlet excited state of 1,4-dicyclobenzene. Biphenyl was used as a codonor. The cyclobutane rings of the initially formed radical cations of I and II cleave to distonic radical cations that react as tertiary alkyl cations and allylic radicals. The results of ab initio MO calculations (STO-3G) are consistent with the observation that the pos. charge is largely associated with the tertiary alkyl moiety while the spin d. is largely distributed over the allylic radical. There was no evidence, exptl. or theor., indicative of a bonding interaction between the cationic and allylic moieties of these distonic radical cations. The cyclobutane ring cleavage is irreversible. The radical cation of III also gives 1:1:1 (nucleophile:cyclopropyl:aromatic) adducts. The regio- and stereochem. of the adducts, and the nucleophile selectivity, are all indicative of nucleophile-assisted cleavage of the radical cation. The radical cation of IV also cleaves to the distonic radical cation. The cyclobutane ring cleavage must be rapid; intramol. 1,5-endo cyclization of the hydroxy group cannot compete.
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Reference:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics