TY - JOUR
T1 - Reaction of enol ethers with zinc carbenoid reagents. Cyclopropanation and subsequent isomerization to allylic ethers
AU - Ryu, Ilhyong
AU - Aya, Tomoyuki
AU - Otani, Shoji
AU - Murai, Shinji
AU - Sonoda, Noboru
PY - 1987/4/10
Y1 - 1987/4/10
N2 - The reactions of enol ethers (ROCC, R = alkyl, silyl) with zinc carbenoid reagents were found to give allylic ethers in several cases along with the expected cyclopropyl ethers. The ratio of these two products was highly dependent on the concentration of the reaction mixture. Thus, the selective formation of each product was conveniently attained by merely changing the amounts of the solvent used. Zinc iodide, a by-product of the reaction, plays a key role in the present cyclopropyl to allylic rearrangement. Ring-opened ionic intermediates are proposed.
AB - The reactions of enol ethers (ROCC, R = alkyl, silyl) with zinc carbenoid reagents were found to give allylic ethers in several cases along with the expected cyclopropyl ethers. The ratio of these two products was highly dependent on the concentration of the reaction mixture. Thus, the selective formation of each product was conveniently attained by merely changing the amounts of the solvent used. Zinc iodide, a by-product of the reaction, plays a key role in the present cyclopropyl to allylic rearrangement. Ring-opened ionic intermediates are proposed.
UR - http://www.scopus.com/inward/record.url?scp=0039329598&partnerID=8YFLogxK
U2 - 10.1016/0022-328X(87)80300-5
DO - 10.1016/0022-328X(87)80300-5
M3 - Article
AN - SCOPUS:0039329598
VL - 321
SP - 279
EP - 290
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
SN - 0022-328X
IS - 3
ER -