TY - JOUR
T1 - Palladium-Catalyzed Substitutions of Allylic Nitro Compounds. Regiochemistry
AU - Tamura, Rui
AU - Kai, Yoshiki
AU - Kakihana, Masato
AU - Havashi, Koji
AU - Tsuji, Masanori
AU - Nakamura, Tsunehiro
AU - Oda, Daihei
PY - 1986/1/1
Y1 - 1986/1/1
N2 - Primary, secondary, and tertiary allylic nitro compounds underwent Pd(0)-catalyzed allylic substitution by stabilized carbanions, secondary amines, and benzenesulfinate ion (PhSO2~). α-nitro olefins also behaved as allylic nitro compounds, via base-catalyzed vinyl allyl rearrangement, and underwent allylic substitution by secondary amines and The regiochemistry of these substitutions was dependent on the structure of the allylic nitro compound and on the steric bulk of the nucleophile. Generally, substitution occurred at the less hindered or least substituted site. In some cases added or generated NaNO2affected the regioselectivity of the allylic substitution of allylic nitro compounds and some allylic acetates by PhSO2‘. Under these conditions, the more sterically hindered allylic sulfones were formed.
AB - Primary, secondary, and tertiary allylic nitro compounds underwent Pd(0)-catalyzed allylic substitution by stabilized carbanions, secondary amines, and benzenesulfinate ion (PhSO2~). α-nitro olefins also behaved as allylic nitro compounds, via base-catalyzed vinyl allyl rearrangement, and underwent allylic substitution by secondary amines and The regiochemistry of these substitutions was dependent on the structure of the allylic nitro compound and on the steric bulk of the nucleophile. Generally, substitution occurred at the less hindered or least substituted site. In some cases added or generated NaNO2affected the regioselectivity of the allylic substitution of allylic nitro compounds and some allylic acetates by PhSO2‘. Under these conditions, the more sterically hindered allylic sulfones were formed.
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U2 - 10.1021/jo00373a008
DO - 10.1021/jo00373a008
M3 - Article
AN - SCOPUS:0000402214
VL - 51
SP - 4375
EP - 4385
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 23
ER -