211-02-9Relevant academic research and scientific papers
Divergent Strategies for the π-Extension of Heteroaryl Halides Using Norbornadiene as an Acetylene Synthon
Jeong, Siyeon,Kim, Eunmin,Kim, Minkyu,Hwang, Ye Ji,Padhi, Birakishore,Choi, Jonghoon,Lee, Yunho,Joo, Jung Min
, p. 9670 - 9676 (2020)
Pd-catalyzed multicomponent coupling reactions of five-membered heteroaryl halides and norbornadiene (NBD) were developed. Either direct addition of (benzo)azoles or 2:1 annulation was achieved depending on the propensity of the intermediate complex to un
Base-Promoted/Gold-Catalyzed Intramolecular Highly Selective and Controllable Detosylative Cyclization
Zhu, Chenghao,Qiu, Lin,Xu, Guangyang,Li, Jian,Sun, Jiangtao
supporting information, p. 12871 - 12875 (2015/09/07)
A highly selective, controllable and synthetically useful base-promoted intramolecular detosylative cyclization of bis-N-tosylhydrazones has been achieved, affording N-containing heterocycles and cyclic olefins under transition-metal-free or gold-catalyzed procedures, respectively. Moreover, an effective and practical metal-free or gold-catalyzed approach to synthesize polycyclic aromatic compounds is also reported. Basic cyclizations: A highly selective, controllable, and synthetically useful base-promoted intramolecular detosylative cyclization of bis-N-tosylhydrazones affords N-containing heterocycles and cyclic olefins under transition-metal-free or gold-catalyzed procedures, respectively. Moreover, an effective and practical metal-free or gold-catalyzed approach to synthesize polycyclic aromatic compounds is also reported.
Unexpected rearrangement during the gas-phase dehalogenation approach to benzodithiophenes
Aitken, R. Alan,Oyewale, Adebayo O.
, p. 19379 - 19381 (2015/04/14)
A range of halogenated methylthiophenes undergo dehalogenative condensation upon FVP over magnesium or calcium to give products including benzodithiophenes; in some cases this involves a novel rearrangement by equilibration of alkenylthienyl radicals via thiophene-fused cyclopropylmethyl intermediates. This journal is
Electrophilic Aromatic Substitution. Part 34. Partial Rate Factors for Detritiation of Dithienobenzene, Dithienobenzene, and Dithienobenzene
Archer, William J.,Cook, Robert,Taylor, Roger
, p. 813 - 820 (2007/10/02)
Dithienobenzene (I), dithienobenzene (II), and dithienobenzene (III), specifically labelled with tritium in each position, have been synthesized.Their rates of protio-detritiation, in either anhydrous trifluoroacetic acid or mixtures of acetic acid and trifluoroacetic acid, have been measured at 70 deg C.The rate-acidity profiles for each compound show that there is weak hydrogen bonding between sulphur and trifluoroacetic acid, and the extent of this is closely similar to that previously found for thienothiophens thereby confirming the general trend observed with sulphur-containing heterocycles viz. that the extent of hydrogen bonding is proportional to the number of sulphur atoms in the aromatic compounds.Partial rate factors for detritiation, free from the effects of hydrogen bonding, are calculated as follows (position and compound in parentheses): 3.42E6 (1)-(I), 1.65E7 (2)-(I), 5.35E5 (4)-(I), 1.525E7 (2)-(II), 4.98E6 (3)-(II), 1.32E6 (4)-(II), 4.59E5 (5)-(II), 2.35E7 (7)-(II), 4.01E6 (8)-(II), 1.96E7 (2)-(III), 3.77E6 (3)-(III), 3.99E5 (4)-(III); the corresponding ?+ values are -0.745, -0.825, -0.655, -0.82, -0.765, -0.70, -0.645, -0.84, -0.755, -0.835, -0.75, and -0.64.The positional reactivity orders both within a given molecule and between molecules are satisfactorily predicted by localization energies calculated by the simple Hueckel method using the parameters αS 1.0, βCS 0.6, these having been found previously to predict correctly the positional reactivities in other sulphur-containing heterocycles.
