Premium
En Route to Dinitroacetylene: Nitro(trimethylsilyl)acetylene and Nitroacetylene Harnessed by Dicobalt Hexacarbonyl
Author(s) -
Windler G. Kenneth,
Zhang MaoXi,
Zitterbart Robert,
Pagoria Philip F.,
Vollhardt K. Peter C.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201200473
Subject(s) - trimethylsilyl , chemistry , nitro , reactivity (psychology) , benzene , acetylene , medicinal chemistry , stoichiometry , ring (chemistry) , crystal structure , photochemistry , organic chemistry , medicine , alkyl , alternative medicine , pathology
Dinitroacetylene and other nitroacetylenes are attractive stoichiometric precursors to high energy‐density materials, but suffer from high reactivity and thermal instability. Herein, we report that nitroacetylenes can be dramatically stabilized in the form of their dicobalt hexacarbonyl complexes. In particular, we describe the syntheses and characterization of the first two transition‐metal complexes of nitroalkynes, [μ‐1‐nitro‐2‐(trimethylsilyl)ethyne‐1,2‐diyl]bis(tricarbonylcobalt)( Co — Co ) and [μ‐1‐nitroethyne‐1,2‐diyl]bis(tricarbonylcobalt)( Co — Co ). The chemistry of these compounds reveals their potential as reaction partners in [2+2+2] cyclotrimerizations, furnishing nitroindane, nitrotetralin, and trinitrobenzene products. The X‐ray crystal structure of 1,3,5‐trinitro‐2,4,6‐tris(trimethylsilyl)benzene presents a distorted, yet planar, aromatic ring.