Deoligomerization: a new route to lactams from unsaturated amides via radical oligomerization.
[reaction: see text] Triethylborane-initiated atom transfer radical oligomerization of N-allyl or N-(3-butenyl)iodoacetamides followed by treatment with hydrochloric acid and subsequent neutralization with K(2)CO(3) led to the formation of the corresponding 5-hydroxyl-substituted delta-lactams or caprolactams, respectively. This oligomerization-deoligomerization sequence serves as an alternative to the corresponding intramolecular cyclization reactions.
Liu
Li
L
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P R China.
Wang
Xing
X
Li
Chaozhong
C
D000577:Amides / Q000737:chemistry*; D002209:Caprolactam / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D000577:Amides; D007769:Lactams; D002209:Caprolactam