Carbocyclization Reaction of omega-Iodo- and 1,omega-Diiodo-1-alkynes without the Loss of Iodine Atoms through a Carbenoid-Chain Process.

Carbocyclization Reaction of omega-Iodo- and 1,omega-Diiodo-1-alkynes without the Loss of Iodine Atoms through a Carbenoid-Chain Process. Research Abstract Details 

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Carbocyclization Reaction of omega-Iodo- and 1,omega-Diiodo-1-alkynes without the Loss of Iodine Atoms through a Carbenoid-Chain Process. Abstract Text:

Toshiro Harada,Keiko Muramatsu,Kenta Mizunashi,Chie Kitano,Daisuke Imaoka,Takayuki Fujiwara,Hiroshi Kataoka,Toshiro Harada,Keiko Muramatsu,Kenta Mizunashi,Chie Kitano,Daisuke Imaoka,Takayuki Fujiwara,Hiroshi Kataoka,

Atom-economical carbocyclization reactions of omega-iodo-1-alkynes and 1,omega-diiodo-1-alkynes to give products with incorporation of iodine atoms is described. Cycloisomerization of 2-(2-propynyloxy)ethyl iodides is initiated by a catalytic amount of LDA to give 3-(iodomethylene)tetrahydrofurans in high yields. Upon treatment of with a catalytic amount of 1-hexynyllithium, 1,omega-diiodo-1-alkynes efficiently undergo cycloisomerization to give (diiodomethylene)cycloalkanes. The diiodomethylene products are also obtained by iodine atom-transfer-type cyclization of omega-iodo-1-alkynes, using 1-iodo-1-hexyne as an external iodine atom source. Bromine atom-transfer and proton-transfer cyclization proceed as well by employing 1-bromo-1-octyne and 1-octyne, respectively. These reactions are proposed to proceed through a carbenoid-chain process involving exo-cyclization of the lithium acetylide intermediates to give Li,I-alkylidene carbenoids. It is shown that the exo-cyclization proceeded stereospecifically through inversion of the stereochemistry at the electrophilic carbon.

Carbocyclization Reaction of omega-Iodo- and 1,omega-Diiodo-1-alkynes without the Loss of Iodine Atoms through a Carbenoid-Chain Process. Publishing Authors By Initials

T Harada,K Muramatsu,K Mizunashi,C Kitano,D Imaoka,T Fujiwara,H Kataoka,T Harada,K Muramatsu,K Mizunashi,C Kitano,D Imaoka,T Fujiwara,H Kataoka,

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Carbocyclization Reaction of omega-Iodo- and 1,omega-Diiodo-1-alkynes without the Loss of Iodine Atoms through a Carbenoid-Chain Process. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: The Journal of organic chemistry

VOLUME: 73

Page Numbers: 249-58

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ISSN: 0022-3263

DAY: 4

MONTH: 12

YEAR: 2007

Carbocyclization Reaction of omega-Iodo- and 1,omega-Diiodo-1-alkynes without the Loss of Iodine Atoms through a Carbenoid-Chain Process. Information

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LANGUAGE: eng

NlmUniqueID: 2985193

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Grant and Affiliation Information for Carbocyclization Reaction of omega-Iodo- and 1,omega-Diiodo-1-alkynes without the Loss of Iodine Atoms through a Carbenoid-Chain Process.

AFFILIATION: Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan.

Country: United States

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MEDLINETA: J Org Chem

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