TY - JOUR
T1 - Synthetic applications of the carbanion walk mechanism
T2 - A novel and facile method for the preparation of 1,3-dimethylenecyclobutane and conjugated vinylallene derivatives.
AU - Braverman, Samuel
AU - Freund, Meir
AU - Reisman, David
AU - Goldberg, Israel
PY - 1986
Y1 - 1986
N2 - Treatment of allenyl sulfone 5 with one half equivalent of n-BuLi in refluxing THF affords a mixture of two dimers: 1,3-dimethylenecyclobutane 7 and vinylallene 6. At 0°C, only the second product is obtained. In contrast, treatment of the same sulfone (5) with a full equivalent of n-BuLi, followed by addition of α,γ,γ-trimethylallenyl phenyl sulfone results in the exclusive formation of 1,3-dimethylenecyclobutane 14, even at low temperatures.
AB - Treatment of allenyl sulfone 5 with one half equivalent of n-BuLi in refluxing THF affords a mixture of two dimers: 1,3-dimethylenecyclobutane 7 and vinylallene 6. At 0°C, only the second product is obtained. In contrast, treatment of the same sulfone (5) with a full equivalent of n-BuLi, followed by addition of α,γ,γ-trimethylallenyl phenyl sulfone results in the exclusive formation of 1,3-dimethylenecyclobutane 14, even at low temperatures.
UR - http://www.scopus.com/inward/record.url?scp=0004848747&partnerID=8YFLogxK
U2 - 10.1016/s0040-4039(00)84242-2
DO - 10.1016/s0040-4039(00)84242-2
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AN - SCOPUS:0004848747
SN - 0040-4039
VL - 27
SP - 1297
EP - 1300
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 11
ER -