Synthesis of novel macrocyclic peroxides by bis(sym-collidine)iodine (I) hexafluorophosphate-mediated cyclization of unsaturated hydroperoxides and unsaturated alcohols

Toyonari Ito; Takahiro Tokuyasu; Araki Masuyama; Masatomo Nojima; Kevin J. McCullough

doi:10.1016/S0040-4020(02)01556-9

Synthesis of novel macrocyclic peroxides by bis(sym-collidine)iodine (I) hexafluorophosphate-mediated cyclization of unsaturated hydroperoxides and unsaturated alcohols

Toyonari Ito
, Takahiro Tokuyasu
, Araki Masuyama
, Masatomo Nojima
, Kevin J. McCullough

School of Engineering & Physical Sciences

Research output: Contribution to journal › Article › peer-review

53 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	525-536
Number of pages	12
Journal	Tetrahedron
Volume	59
Issue number	4
DOIs	https://doi.org/10.1016/S0040-4020(02)01556-9
Publication status	Published - 20 Jan 2003

Keywords

Iodonium ion-mediated cyclization
Macrocyclic peroxide
Unsaturated alcohol
Unsaturated hydroperoxide

Access to Document

10.1016/S0040-4020(02)01556-9

Cite this

@article{9f989bc717c94e749774b432648442bc,

title = "Synthesis of novel macrocyclic peroxides by bis(sym-collidine)iodine (I) hexafluorophosphate-mediated cyclization of unsaturated hydroperoxides and unsaturated alcohols",

abstract = "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. {\textcopyright} 2003 Elsevier Science Ltd. All rights reserved.",

keywords = "Iodonium ion-mediated cyclization, Macrocyclic peroxide, Unsaturated alcohol, Unsaturated hydroperoxide",

author = "Toyonari Ito and Takahiro Tokuyasu and Araki Masuyama and Masatomo Nojima and McCullough, \{Kevin J.\}",

year = "2003",

month = jan,

day = "20",

doi = "10.1016/S0040-4020(02)01556-9",

language = "English",

volume = "59",

pages = "525--536",

journal = "Tetrahedron",

issn = "1464-5416",

publisher = "Elsevier Ltd",

number = "4",

}

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 - https://www.scopus.com/pages/publications/0037454656

U2 - 10.1016/S0040-4020(02)01556-9

DO - 10.1016/S0040-4020(02)01556-9

M3 - Article

SN - 1464-5416

VL - 59

SP - 525

EP - 536

JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

Synthesis of novel macrocyclic peroxides by bis(sym-collidine)iodine (I) hexafluorophosphate-mediated cyclization of unsaturated hydroperoxides and unsaturated alcohols

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this