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Controlled Rearrangement of 2,3‐Dilithio‐1,3‐butadienes to 2,5‐Dilithio‐1,3‐butadienes: Synthesis of 2‐Isopropylidene‐2,5‐dihydrosilols
Author(s) -
Maercker Adalbert,
Wunderlich H.,
Girreser Ulrich
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199805)1998:5<793::aid-ejoc793>3.0.co;2-3
Subject(s) - chemistry , medicinal chemistry , conjugated system , rearrangement reaction , sigmatropic reaction , stereochemistry , organic chemistry , catalysis , polymer
3,4‐Dilithio‐2,5‐dimethyl‐2,4‐hexadiene ( 4a ) rearranges to the cross‐conjugated 2,5‐dimethylhexadienediyl dianion 11a . A mechanistic investigation proves the intermolecularity of this rearrangement, which is also observed when starting from 4b . The 3‐lithio‐2,5‐dimethylhexadienyl anion 10a with one vinyllithium and one allyllithium group, is a true intermediate in this rearrangement, its synthetic potential is employed in the reaction with dichlorosilanes to form 2‐isopropylidene‐2,5‐dihydrosilols 8 .