Cyclopropylcarbinyl radical-mediated ring expansion to seven-membered carbocycles

Eric J. Kantorowski, Babak Borhan, Saman Nazarian, Mark J. Kurth

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Radical-mediated ring expansion methodology is presented wherein 7- membered carbocycles can be prepared from the corresponding xanthate derivatives of bicyclo[4.1.0]heptan-1-methanol. In certain systems, an intermediate cycloheptyl radical appears to be kinetically favored over the cyclohexyl radical, but the direction of cyclopropylcarbinyl radical fragmentation is subject to substitution about the bicyclo[4.1.0]heptan-1- methyl ring.

Original languageEnglish (US)
Pages (from-to)2483-2486
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number17
DOIs
StatePublished - Apr 23 1998

Fingerprint

Methanol
Substitution reactions
Derivatives
Direction compound

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Cyclopropylcarbinyl radical-mediated ring expansion to seven-membered carbocycles. / Kantorowski, Eric J.; Borhan, Babak; Nazarian, Saman; Kurth, Mark J.

In: Tetrahedron Letters, Vol. 39, No. 17, 23.04.1998, p. 2483-2486.

Research output: Contribution to journalArticle

Kantorowski, Eric J. ; Borhan, Babak ; Nazarian, Saman ; Kurth, Mark J. / Cyclopropylcarbinyl radical-mediated ring expansion to seven-membered carbocycles. In: Tetrahedron Letters. 1998 ; Vol. 39, No. 17. pp. 2483-2486.
@article{e3115dbfe781449a9709eeeecdb8efa0,
title = "Cyclopropylcarbinyl radical-mediated ring expansion to seven-membered carbocycles",
abstract = "Radical-mediated ring expansion methodology is presented wherein 7- membered carbocycles can be prepared from the corresponding xanthate derivatives of bicyclo[4.1.0]heptan-1-methanol. In certain systems, an intermediate cycloheptyl radical appears to be kinetically favored over the cyclohexyl radical, but the direction of cyclopropylcarbinyl radical fragmentation is subject to substitution about the bicyclo[4.1.0]heptan-1- methyl ring.",
author = "Kantorowski, {Eric J.} and Babak Borhan and Saman Nazarian and Kurth, {Mark J.}",
year = "1998",
month = "4",
day = "23",
doi = "10.1016/S0040-4039(98)00311-6",
language = "English (US)",
volume = "39",
pages = "2483--2486",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "17",

}

TY - JOUR

T1 - Cyclopropylcarbinyl radical-mediated ring expansion to seven-membered carbocycles

AU - Kantorowski, Eric J.

AU - Borhan, Babak

AU - Nazarian, Saman

AU - Kurth, Mark J.

PY - 1998/4/23

Y1 - 1998/4/23

N2 - Radical-mediated ring expansion methodology is presented wherein 7- membered carbocycles can be prepared from the corresponding xanthate derivatives of bicyclo[4.1.0]heptan-1-methanol. In certain systems, an intermediate cycloheptyl radical appears to be kinetically favored over the cyclohexyl radical, but the direction of cyclopropylcarbinyl radical fragmentation is subject to substitution about the bicyclo[4.1.0]heptan-1- methyl ring.

AB - Radical-mediated ring expansion methodology is presented wherein 7- membered carbocycles can be prepared from the corresponding xanthate derivatives of bicyclo[4.1.0]heptan-1-methanol. In certain systems, an intermediate cycloheptyl radical appears to be kinetically favored over the cyclohexyl radical, but the direction of cyclopropylcarbinyl radical fragmentation is subject to substitution about the bicyclo[4.1.0]heptan-1- methyl ring.

UR - http://www.scopus.com/inward/record.url?scp=0032559994&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032559994&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(98)00311-6

DO - 10.1016/S0040-4039(98)00311-6

M3 - Article

AN - SCOPUS:0032559994

VL - 39

SP - 2483

EP - 2486

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 17

ER -