C-C bond formation at ozonide rings by substitution of chlorinated ozonides

Karl Griesbaum; Ralf Olaf Quinkert; Kevin J. McCullough

doi:10.1002/ejoc.200400167

C-C bond formation at ozonide rings by substitution of chlorinated ozonides

Karl Griesbaum, Ralf Olaf Quinkert, Kevin J. McCullough

School of Engineering & Physical Sciences

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

3 Citations (Scopus)

Abstract

The TiCl₄-mediated substitution of 3-chloro-3,5- bis(chloromethyl)-5-methyl-1,2,4-trioxolane (1) with 1-(trimethylsilyloxy) cyclopentene (4), 2-methyl-1-(trimethylsilyloxy)propene (6) and allyltrimethylsilane (12) gave the corresponding 2-oxocyclopentyl-, 1,1-dimethyl-2-oxo-ethyl- and allyl-substituted ozonides 5, 7 and 13, respectively. Substitution of 3,5-dichloro-3,5-bis(chloromethyl)-1,2,4- trioxolane (2) with allyl-trimethylsilane (12) gave the diallyl-substituted ozonide 14. Ozonolysis of the allyl-substituted ozonide 13 provided the corresponding diozonide 17, and ozonolysis of the diallyl-substituted ozonide 14 provided the corresponding diozonide 18 and triozonide 19. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Original language	English
Pages (from-to)	3657-3662
Number of pages	6
Journal	European Journal of Organic Chemistry
Issue number	17
DOIs	https://doi.org/10.1002/ejoc.200400167
Publication status	Published - 27 Aug 2004

Keywords

C-C coupling
Ozonolysis
Substitution
Synthetic methods

Access to Document

10.1002/ejoc.200400167

Cite this

@article{dc4cfbe6ecb3477c8ebdb83525da4123,

title = "C-C bond formation at ozonide rings by substitution of chlorinated ozonides",

abstract = "The TiCl4-mediated substitution of 3-chloro-3,5- bis(chloromethyl)-5-methyl-1,2,4-trioxolane (1) with 1-(trimethylsilyloxy) cyclopentene (4), 2-methyl-1-(trimethylsilyloxy)propene (6) and allyltrimethylsilane (12) gave the corresponding 2-oxocyclopentyl-, 1,1-dimethyl-2-oxo-ethyl- and allyl-substituted ozonides 5, 7 and 13, respectively. Substitution of 3,5-dichloro-3,5-bis(chloromethyl)-1,2,4- trioxolane (2) with allyl-trimethylsilane (12) gave the diallyl-substituted ozonide 14. Ozonolysis of the allyl-substituted ozonide 13 provided the corresponding diozonide 17, and ozonolysis of the diallyl-substituted ozonide 14 provided the corresponding diozonide 18 and triozonide 19. {\textcopyright} Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.",

keywords = "C-C coupling, Ozonolysis, Substitution, Synthetic methods",

author = "Karl Griesbaum and Quinkert, {Ralf Olaf} and McCullough, {Kevin J.}",

year = "2004",

month = aug,

day = "27",

doi = "10.1002/ejoc.200400167",

language = "English",

pages = "3657--3662",

journal = "European Journal of Organic Chemistry",

issn = "1099-0690",

publisher = "Wiley-VCH Verlag",

number = "17",

}

TY - JOUR

T1 - C-C bond formation at ozonide rings by substitution of chlorinated ozonides

AU - Griesbaum, Karl

AU - Quinkert, Ralf Olaf

AU - McCullough, Kevin J.

PY - 2004/8/27

Y1 - 2004/8/27

N2 - The TiCl4-mediated substitution of 3-chloro-3,5- bis(chloromethyl)-5-methyl-1,2,4-trioxolane (1) with 1-(trimethylsilyloxy) cyclopentene (4), 2-methyl-1-(trimethylsilyloxy)propene (6) and allyltrimethylsilane (12) gave the corresponding 2-oxocyclopentyl-, 1,1-dimethyl-2-oxo-ethyl- and allyl-substituted ozonides 5, 7 and 13, respectively. Substitution of 3,5-dichloro-3,5-bis(chloromethyl)-1,2,4- trioxolane (2) with allyl-trimethylsilane (12) gave the diallyl-substituted ozonide 14. Ozonolysis of the allyl-substituted ozonide 13 provided the corresponding diozonide 17, and ozonolysis of the diallyl-substituted ozonide 14 provided the corresponding diozonide 18 and triozonide 19. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

AB - The TiCl4-mediated substitution of 3-chloro-3,5- bis(chloromethyl)-5-methyl-1,2,4-trioxolane (1) with 1-(trimethylsilyloxy) cyclopentene (4), 2-methyl-1-(trimethylsilyloxy)propene (6) and allyltrimethylsilane (12) gave the corresponding 2-oxocyclopentyl-, 1,1-dimethyl-2-oxo-ethyl- and allyl-substituted ozonides 5, 7 and 13, respectively. Substitution of 3,5-dichloro-3,5-bis(chloromethyl)-1,2,4- trioxolane (2) with allyl-trimethylsilane (12) gave the diallyl-substituted ozonide 14. Ozonolysis of the allyl-substituted ozonide 13 provided the corresponding diozonide 17, and ozonolysis of the diallyl-substituted ozonide 14 provided the corresponding diozonide 18 and triozonide 19. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

KW - C-C coupling

KW - Ozonolysis

KW - Substitution

KW - Synthetic methods

U2 - 10.1002/ejoc.200400167

DO - 10.1002/ejoc.200400167

M3 - Article

SN - 1099-0690

SP - 3657

EP - 3662

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 17

ER -

C-C bond formation at ozonide rings by substitution of chlorinated ozonides

Abstract

Keywords

Access to Document

Fingerprint

Cite this