TY - JOUR
T1 - Synthesis of novel macrocyclic peroxides by bis(sym-collidine)iodine (I) hexafluorophosphate-mediated cyclization of unsaturated hydroperoxides and unsaturated alcohols
AU - Ito, Toyonari
AU - Tokuyasu, Takahiro
AU - Masuyama, Araki
AU - Nojima, Masatomo
AU - McCullough, Kevin J.
PY - 2003/1/20
Y1 - 2003/1/20
N2 - Bis(sym-collidine)iodine (I) hexafluorophosphate-mediated cyclization of unsaturated hydroperoxides, prepared by a variety of different methods, afforded the corresponding 10- to 20-membered macrocyclic peroxides having two or three peroxide units located within one ring in moderate yields. By analogy, cyclization of unsaturated alcohols having one or two peroxide bond in the chain afforded the corresponding cyclic ethers. The efficiency of the latter reactions were found to be a function of the structure of the alcohols. © 2003 Elsevier Science Ltd. All rights reserved.
AB - Bis(sym-collidine)iodine (I) hexafluorophosphate-mediated cyclization of unsaturated hydroperoxides, prepared by a variety of different methods, afforded the corresponding 10- to 20-membered macrocyclic peroxides having two or three peroxide units located within one ring in moderate yields. By analogy, cyclization of unsaturated alcohols having one or two peroxide bond in the chain afforded the corresponding cyclic ethers. The efficiency of the latter reactions were found to be a function of the structure of the alcohols. © 2003 Elsevier Science Ltd. All rights reserved.
KW - Iodonium ion-mediated cyclization
KW - Macrocyclic peroxide
KW - Unsaturated alcohol
KW - Unsaturated hydroperoxide
UR - http://www.scopus.com/inward/record.url?scp=0037454656&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(02)01556-9
DO - 10.1016/S0040-4020(02)01556-9
M3 - Article
VL - 59
SP - 525
EP - 536
JO - Tetrahedron
JF - Tetrahedron
IS - 4
ER -