1198-20-5Relevant academic research and scientific papers
Electronic Control of Stereoselectivity in the Metal Hydride Reductions of 1,2,3,4-Tetrahydro-1,4-methanonaphthalen-9-ones
Okada, Keiji,Tomita, Seiji,Oda, Masaji
, p. 459 - 468 (1989)
Stereoselectivity in the metal hydride reduction of a series of substituted 1,2,3,4-tetrahydro-1,4-methanonaphthalen-9-ones was investigated in relation to their homoconjugation character.The observed stereoselectivity sequence was found to be parallel wi
Bridged aromatic alkenes for the study of carbocation-π interaction
Spencer, Thomas A.,Popovici-Müller, Janeta,van Beusichem, Bobbijo,MacMillan, Celeste Viscardi,Lavey, Carolee F.,Sin, Jessica M.,Ditchfield, Robert
scheme or table, p. 4441 - 4451 (2010/07/06)
Toward the goal of gaining further insight into carbocation-π interactions, bridged-ring aromatic alkene model systems are being investigated in which one isomer will permit π complexation of an intramolecular tertiary carbocation with a benzene ring, but
X-ray crystal structures of a benzonorbornenyl cation and of a protonated benzonorbornenol
Laube, Thomas
, p. 10904 - 10912 (2007/10/03)
The crystal structure of the 9-methylbenzonorbornenyl cation Me-1 + shows a relatively strong interaction between the sp 2-hybridized carbon atom C9 and the aromatic ring (C4a-C9 ≡ C8a-C9 = 1.897(10) A). The anion Sb2F11- is refined as rotationally disordered along the Sb...Sb axis. In sharp contrast to the findings about Me-1+, the protonated anti-benzonorbornenol 5+ is essentially an oxonium ion with only weak interaction between the C9 bridge and the aromatic ring despite the fact that it is already a positively charged ion, which upon loss of a water molecule is expected to give the parent cation H-1+. The hydrogen atoms on the oxonium O atom are involved in strong hydrogen bonds to chlorosulfonate anions and probably partially disordered despite the large estimated pKa differences between the corresponding acid-base pairs. The experimentally determined cation structures are compared with structures computed by DFT methods. Detailed experimental procedures are given.
