Intramolecularly Group 15 Stabilized Aryltellurenyl Halides and Triflates | Zendy

Truong Giang | Zendy; Emanuel Hupf | Zendy; Andreas Nordheider | Zendy; Enno Lork | Zendy; Alexandra M. Z. Slawin | Zendy; Sergey G. Makarov | Zendy; Sergey Yu. Ketkov | Zendy; Stefan Mebs | Zendy; J. Derek Woollins | Zendy; Jens Beckmann | Zendy

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Intramolecularly Group 15 Stabilized Aryltellurenyl Halides and Triflates

Author(s) -

Truong Giang,

Emanuel Hupf,

Andreas Nordheider,

Enno Lork,

Alexandra M. Z. Slawin,

Sergey G. Makarov,

Sergey Yu. Ketkov,

Stefan Mebs,

J. Derek Woollins,

Jens Beckmann

Publication year - 2015

Publication title -

organometallics

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.231

H-Index - 172

eISSN - 1520-6041

pISSN - 0276-7333

DOI - 10.1021/acs.organomet.5b00813

Subject(s) - chemistry , metathesis , aryl , triflic acid , salt metathesis reaction , stereochemistry , crystal structure , crystallography , nuclear magnetic resonance spectroscopy , halide , medicinal chemistry , inorganic chemistry , organic chemistry , polymerization , alkyl , catalysis , polymer

The Deutsche Forschungsgemeinschaft (DFG) is gratefully acknowledged for financial support. The energy decomposition and deformation electron density analyses were carried out within the framework of the Project 14-13-00832 supported by the Russian Science Foundation.The preparation of a series of functionalized peri-substituted acenaphthyl compounds 6-Ph2E-Ace-5-Br (1, E = As; 2, E = Sb), 6-Ph2As-Ace-5-TeMes (3), 5-I-Ace-6-TeMes (4), 6-Ph2Sb-Ace-5-TeMes (5), (6-Ph2P-Ace-5)2Te (6), [6-R2E-Ace-5-Te]X (7, E = P, R = Ph, X = Cl; 8, E = P, R = i-Pr, X = Cl; 9, E = P, R = i-Pr, X = Br; 10, E = P, R = i-Pr, X = I; 11, E = P, R = i-Pr, X = ½ (TeI6); 12, E = P, R = i-Pr, X = I3; 13, E = P, R = Ph, X = O3SCF3; 14, E = As, R = Ph, X = O3SCF3; 15, E = Sb, R = Ph, X = O3SCF3) and [6-PhSb-Ace-5-TeMes]O3SCF3 (16) was reported (Ace = acenaphthyl). The synthesis of 7-15 was either achieved by salt metathesis reaction of 5-i-Pr2P-Ace-6-Li with TeCl2∙TMTU (8), TeBr2∙TMTU (9) and TeI4 (10 + 11) or by the aryl cleavage reaction of 6-R2E-Ace-5-TeMes (E = P, As, Sb; R = Ph, i-Pr) with HgCl2 (7), I2 (12) and HO3SCF3 (13-15). The reaction of 5 with triflic acid gave also rise to the formation of [6-PhSb-Ace-5-TeMes]O3SCF3 (16). All compounds have been characterized by multinuclear NMR spectroscopy and single crystal X-ray diffraction. Complementary DFT studies including relaxed potential energy scans (PES) and subsequent topological analysis of the resulting electron and pair densities according to the AIM and ELI-D partitioning schemes are performed for the aryltellurenyl chlorides [6-Ph2P-Ace-5-Te]Cl, [8-Me2N-Nap-1-Te]Cl and [8-Me2P-Nap-1-Te]Cl in the gas phase and in MeCN solution, whereby the Te-Cl distances were systematically varied. The same analyses were carried out for the fully optimized [6-R2E-Ace-5-Te]+ cations (E = P, As, Sb) and compared to those of the previously studied intermolecularly stabilized [R3ETeMes]+ cations (E = P, As, Sb).PostprintPeer reviewe

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