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Zur Reaktivität des Silaethens Me 2 Si = C(SiMe 3 ) 2 : Relative Geschwindigkeiten der Diels‐Alder‐Reaktionen mit organischen Dienen 1,2)
Author(s) -
Wiberg Nils,
Wagner Susanne,
Fischer Gerd
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911240916
Subject(s) - chemistry , isoprene , steric effects , diene , cycloaddition , medicinal chemistry , reactivity (psychology) , diels–alder reaction , stereochemistry , organic chemistry , catalysis , medicine , natural rubber , alternative medicine , pathology , copolymer , polymer
On the Reactivity of the Silaethene Me 2 Si = C(SiMe 3 ) 2 : Relative Rates of Diels‐Alder Reactions with Organic Dienes 1,2) [4 + 2] Cycloaddition of dienes to silaethene Me 2 Si = C(SiMe 3 ) 2 is accelerated in the directions: (i) butadiene < isoprene < CH 2 = CR – CH = CH 2 with R = CH 2 SiMe 2 CH‐ (SiMe 3 ) 2 (increase in electron donation of the diene substiuents), (ii) trans ‐piperylene < 2,3‐dimethylbutadiene (DMB) < isoprene (decrease in steric hindrance of diene substituents), (iii) cis ‐piperylene or cis,trans ‐hexadiene < trans ‐piperylene and trans,trans ‐hexadiene (decrease in equilibrium concentration of the cisoid conformer).