Lewis Acid-Mediated Ring-Opening Reactions of trans-2-Aroyl-3-styrylcyclopropane-1,1-dicarboxylates: Access to Cyclopentenes and E,E-1,3-Dienes

DOI: 10.1021/acs.joc.7b02335

Source and publish data:

Journal of Organic Chemistry p. 571 - 577 (2018)

Update date:2022-08-03

Topics:

Authors:

Thangamani, Murugesan

Srinivasan, Kannupal

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1021/acs.joc.7b02335

The ring-opening reaction of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates was investigated with different Lewis acids. With SnCl₄, the cyclopropane dicarboxylates afforded cyclopentene derivatives through ring opening followed by cyclization (vinylcyclopropane-cyclopentene rearrangement). With TiCl₄, they furnished E,E-1,3-diene derivatives stereoselectively via ring opening followed by proton elimination.

Full text of DOI:10.1021/acs.joc.7b02335

Products guided by the article

Product name:2,4-Pentadien-1-one, 1-(4-chlorophenyl)-5-(4-methylphenyl)-

Cas No:62643-84-9

R&D Labs maybe for 62643-84-9

Hubei Danao Pharmaceutical Co.,Ltd.

website:http://www.danaopharm.com

Contact:+86-719-5251167

Address:Fandan Road,Danjiangkou,Hubei
Beijing eternalchem Co,. Ltd

Contact:+86-10-59484199

Address:No.58-A1026 Liangguan Street
Antaeus Bio-technology Co., LTD(expird)

Contact:021-31252569

Address:shanghai pudong
TC CHEMICALS CO.,LTD

Contact:0550-7041128 0550-7090578

Address:Wangdian Street,Xinjie Town
Taiwan Surfactant Corp.

Contact:886 2 2541 0022

Address:8 Fl., No. 11, Sec. 1, Chung Shan North Rd., Taipei, Taiwan R.O.C.

Relevant to this article

Microwave-Assisted [3 + 2] Cycloadditions of Azomethine Ylides

Doi:10.1021/ol0361195
(2003)
Protoberberines from Reissert- compounds. Part IX [1]. An alternative approach to dibenzoquinolizine- and isoquinonaphthyridin-13a-carboxylic acids, a novel synthesis of alangimarine

Doi:10.1007/s00706-004-0231-5
(2005)
Doi:10.1021/jo00438a020
(1977)
Amino-acids and peptides. Part XVII. Synthesis of cyclo-[(O-t-butyl)-L-seryl-beta-alanyl-glycyl-(O-methyl)-L-beta-aspartyl], and observations on the rearrangement of beta-aspartyl peptides esters.

Doi:10.1039/P19760002014
(1976)
Electrochemical C-H cyanation of electron-rich (Hetero)arenes

Doi:10.1002/chem.201802247
(2018)
Doi:10.1007/BF00900925
(1977)

Article Doi