Literature DB >> 29711380

Rhodium(I)-Catalyzed Regioselective Ring- Expanding Rearrangement of Allenylcyclopropanes into Methylenecyclopentenes.

Minoru Hayashi1, Tadashi Ohmatsu1, Yun-Ping Meng1, Kazuhiko Saigo1.   

Abstract

A highly regioselective C-C bond cleavage of the cyclopropane rings occurs in substituted allenylcyclopropanes in the presence of cationic rhodium(I) complexes. Thus, ring expansion of readily accessible allenylcyclopropanes can be achieved to give 3-methylenecyclopentenes, which could have applications as multifunctional synthetic building blocks. © 1998 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  Allenes; Carbocycles; Rearrangements; Rhodium; Small ring systems

Year:  1998        PMID: 29711380     DOI: 10.1002/(SICI)1521-3773(19980403)37:6<837::AID-ANIE837>3.0.CO;2-R

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  4 in total

1.  Rhodium-catalyzed ring expansion of cyclopropanes to seven-membered rings by 1,5 C-C bond migration.

Authors:  Xiaoxun Li; Min Zhang; Dongxu Shu; Patrick J Robichaux; Suyu Huang; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-09       Impact factor: 15.336

2.  Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp2)-H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes.

Authors:  Yidong Wang; Sarah G Scrivener; Xiao-Dong Zuo; Ruihan Wang; Philip N Palermo; Ethan Murphy; Austin C Durham; Yi-Ming Wang
Journal:  J Am Chem Soc       Date:  2021-09-07       Impact factor: 16.383

3.  Rhodium-catalyzed carbonylation of cyclopropyl substituted propargyl esters: a tandem 1,3-acyloxy migration [5 + 1] cycloaddition.

Authors:  Dongxu Shu; Xiaoxun Li; Min Zhang; Patrick J Robichaux; Ilia A Guzei; Weiping Tang
Journal:  J Org Chem       Date:  2012-07-25       Impact factor: 4.354

4.  Rh(II)-Catalyzed Alkynylcyclopropanation of Alkenes by Decarbenation of Alkynylcycloheptatrienes.

Authors:  Mauro Mato; Marc Montesinos-Magraner; Arnau R Sugranyes; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2021-07-08       Impact factor: 15.419

  4 in total

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