1991
DOI: 10.1021/ja00021a037
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A carbene to biradical rearrangement: reaction paths from (8-methyl-1-naphthyl)carbene to acenaphthene

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Cited by 20 publications
(19 citation statements)
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“…If 1,8-naphthoquinodimethane was formed by a two photon process, the main absorption bands would be expected to appear in the region of 350-300 nm in addition to a weak band around 500 nm. 35 In this case, the bands in both these regions should behave in the same way when O 2 is present; however, the observed decays were different (Fig. 6).…”
Section: (A)]mentioning
confidence: 75%
“…If 1,8-naphthoquinodimethane was formed by a two photon process, the main absorption bands would be expected to appear in the region of 350-300 nm in addition to a weak band around 500 nm. 35 In this case, the bands in both these regions should behave in the same way when O 2 is present; however, the observed decays were different (Fig. 6).…”
Section: (A)]mentioning
confidence: 75%
“…On the other hand, ionization tends to reduce the thermochemical driving force for bond formation; this is reflected in the fact that the ionization potential of the diradical (e.g. PD, n = 3) is generally much lower than that of the corresponding closed-shell product (1). Moreover, state symmetry may impose reaction barriers in radical cation interconversions that do not exist for their neutral counterparts.…”
Section: Introductionmentioning
confidence: 99%
“…The lack of reactivity of triplet nitrenes toward H-abstraction, even for intramolecular reactions, contrasts with the reactivity of triplet carbenes. This uniqueness has been interpreted as a result of thermodynamic and electronic factors. Triplet nitrenes are ∼20 kcal mol –1 more stable than the comparably substituted triplet carbenes. Moreover, the singlet–triplet gap (Δ E S‑T ) in nitrenes is generally much larger than in carbenes.…”
mentioning
confidence: 99%