1460-59-9Relevant articles and documents
An efficient synthesis of dibenzocycloocta-4a,6a,-diene-5,11-diyne and its precursors
Chaffins, Sterling,Brettreich, Michael,Wudl, Fred
, p. 1191 - 1194 (2002)
Two efficient syntheses of dibenzocyclooctadienediyne 1 were developed employing known reactions, which utilize commercially available reagents. Both methods are an improvement on known syntheses resulting in 41% and 43% overall yields. The latter method also offers an efficient synthesis of dibenzocyclooctatetraene 9, which is one of the key reagents now commercially unavailable.
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Cava,M.P. et al.
, p. 1861 - 1863 (1963)
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Jensen,Coleman
, p. 7,10 (1959)
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Organic Sonochemistry. New Ultrasonically Accelerated Reactions Involving Lithium
Boudjouk, Philip,Sooriyakumaran, Ratnasabapathy,Han, Byung-Hee
, p. 2818 - 2819 (1986)
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Observation of Reactive o-Quinodimethanes by Flow NMR
Trahanovsky, Walter S.,Chou, C. -H.,Fischer, D. R.,Gerstein, B. C.
, p. 6579 - 6581 (1988)
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Defoin et al.
, p. 83,84,87,88,92 (1978)
Loudon et al.
, p. 1733 (1970)
Bornstein et al.
, p. 1499,1503 (1967)
Iridium-Triggered Allylcarbamate Uncaging in Living Cells
Singh, Neelu,Gupta, Ajay,Prasad, Puja,Mahawar, Pritam,Gupta, Shalini,Sasmal, Pijus K.
supporting information, p. 12644 - 12650 (2021/09/06)
Designing a metal catalyst that addresses the major issues of solubility, stability, toxicity, cell uptake, and reactivity within complex biological milieu for bioorthogonal controlled transformation reactions is a highly formidable challenge. Herein, we report an organoiridium complex that is nontoxic and capable of the uncaging of allyloxycarbonyl-protected amines under biologically relevant conditions and within living cells. The potential applications of this uncaging chemistry have been demonstrated by the generation of diagnostic and therapeutic agents upon the activation of profluorophore and prodrug in a controlled fashion within HeLa cells, providing a valuable tool for numerous potential biological and therapeutic applications.
Mechanism of the Bis(imino)pyridine-Iron-Catalyzed Hydromagnesiation of Styrene Derivatives
Neate, Peter G. N.,Greenhalgh, Mark D.,Brennessel, William W.,Thomas, Stephen P.,Neidig, Michael L.
supporting information, p. 10099 - 10108 (2019/07/04)
Iron-catalyzed hydromagnesiation of styrene derivatives offers a rapid and efficient method to generate benzylic Grignard reagents, which can be applied in a range of transformations to provide products of formal hydrofunctionalization. While iron-catalyzed methodologies exist for the hydromagnesiation of terminal alkenes, internal alkynes, and styrene derivatives, the underlying mechanisms of catalysis remain largely undefined. To address this issue and determine the divergent reactivity from established cross-coupling and hydrofunctionalization reactions, a detailed study of the bis(imino)pyridine iron-catalyzed hydromagnesiation of styrene derivatives is reported. Using a combination of kinetic analysis, deuterium labeling, and reactivity studies as well as in situ 57Fe M?ssbauer spectroscopy, key mechanistic features and species were established. A formally iron(0) ate complex [iPrBIPFe(Et)(CH2a?CH2)]- was identified as the principle resting state of the catalyst. Dissociation of ethene forms the catalytically active species which can reversibly coordinate the styrene derivative and mediate a direct and reversible β-hydride transfer, negating the necessity of a discrete iron hydride intermediate. Finally, displacement of the tridentate bis(imino)pyridine ligand over the course of the reaction results in the formation of a tris-styrene-coordinated iron(0) complex, which is also a competent catalyst for hydromagnesiation.
