New Reactions of a Dibenzo[a,e]pentalene
✍ Scribed by Masaichi Saito; Michio Nakamura; Tomoyuki Tajima
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- English
- Weight
- 540 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0947-6539
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✦ Synopsis
Abstract
Reduction of dibenzo[a,e]pentalene 3 (denoted as dibenzopentalene hereafter) with excess lithium gave dilithium dibenzopentalenide 1. Since oxidation of 1 with iodine gave 3, redox behavior between 1 and 3 is controllable and reversible. Reaction of 3 with methyllithium gave lithium 5‐methyldibenzopentalenide 5, the formation of which was evidenced by some trapping experiments and X‐ray crystallographic analysis. Reactions of 3 with halogens gave 5,10‐dihalodibenzopentalenes, 8 and 9. Some optical properties of novel dibenzopentalene derivatives are also demonstrated.
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152-155"C, which is recyclized to (3a) by phosgene in the presence of a tertiary amine. 3,4-Dichloroaniline reacts with (3a) even at ca. 20"C, giving the monothiotriuret (6a), m.p. 163°C. (3a) can be prepared from (la) and phenoxycarbonyl isocyanate in boiling toluene even in absence of a tertiary b
## Abstract The kinetics of the hydride transfer reactions of the dibenzo‐tropylium ion (2) with dimethylphenylsilane (5) and triphenylsilane (6) were used to determine its electrophilicity parameter __E__ = ‐0.71. The nucleophiles 7–9 react 10–40 times faster with 2 than expected from the linear f