N-Heterocyclic carbenes from ylides of indolyl-imidazolium, azaindolyl-imidazolium, and indolyl-triazolium salts, and their borane adducts
Abstract Indol-2-yl-imidazolium salts were deprotonated at N1 of the indole ring to give ylides. Their tautomeric N-heterocyclic carbenes (NHCs) were trapped by sulfur to give imidazole-2-thiones. Treatment of the ylides with triethylborane resulted in the formation of zwitterionic borane adducts. An analogous sequence of reactions was performed with 8-azaindol-2-yl-imidazolium salts, which served as precursor to prepare first representatives of a new heterocyclic ring system on reaction of their NHC-tautomers with triethylborane. Similarly, an indol-2-yl-1,2,4-triazolium salt was examined with respect to ylide–NHC tautomerism and trapping reactions. A nucleophilic ring transformation of in…
<title>Miniaturized objective lens for a photoelectron emission microscope</title>
Photoemission electron microscopy (PEEM) has turned out to be one of the most promising methods for surface analysis in the recent years. It is a full field imaging technique based on the emission of secondary electrons by far ultraviolet light or X-rays. The emission intensity of secondary electrons is critically dependent upon the acceptance angle of the incident radiation. However, the size of the microscope restricts this angle substantially. Miniaturizing the objective lens of the microscope reduces the restriction of the acceptance angle and improves the performance of the PEEM considerably. We report on the fabrication of a miniaturized objective lens containing the extraction electr…
Synthesis of 2-anilinobenzimidates, anthranilamides, and 2,3-dihydroquinazolin-4(1H)-ones from N-heterocyclic carbenes of indazole
N-Heterocyclic carbenes of indazole (indazol-3-ylidenes), which are substituted at N1 with aromatics were generated in situ from the corresponding indazolium salts. At 60 °C the indazol-3-ylidenes underwent a ring-opening under N–N bond cleavage to intermediary N-(6-methylenecyclohexa-2,4-dien-1-ylidene)anilines. Trapping of these intermediates by alcohols proved to be a convenient method for the preparation of 2-anilinobenzimidates, which have scarcely been described in the literature. The reaction temperature avoids carbene dimerization, which occurs at −80 °C or rearrangement of the ring-opened intermediate to acridines, which affords 100 °C. Water converted the ring-opened products into…
CCDC 1029374: Experimental Crystal Structure Determination
Related Article: Zong Guan, Kai Hillrichs, Cemre Ünlü, Kari Rissanen, Martin Nieger, Andreas Schmidt|2015|Tetrahedron|71|276|doi:10.1016/j.tet.2014.11.054
CCDC 1018185: Experimental Crystal Structure Determination
Related Article: Nazar Pidlypnyi, Sebastian Wolf, Ming Liu, Kari Rissanen, Martin Nieger, Andreas Schmidt|2014|Tetrahedron|70|8672|doi:10.1016/j.tet.2014.09.035