Literature DB >> 19260696

A practical, two-step synthesis of 2-substituted 1,3-butadienes.

Sushmita Sen1, Swapnil Singh, Scott McN Sieburth.   

Abstract

A two-step procedure for preparing 2-alkyl-1,3-butadienes is described. Cuprate addition to commercially available 1,4-dibromo-2-butene yields 3-alkyl-4-bromo-1-butene, a product of S(N)2' substitution. Dehydrohalogenation gives 2-alkyl-1,3-butadienes.

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Year:  2009        PMID： 19260696      PMCID： PMC2764119          DOI： 10.1021/jo802737x

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  10 in total

1.  A boronic ester annulation strategy for diversity-oriented organic synthesis.

Authors:  Glenn C Micalizio; Stuart L Schreiber
Journal:  Angew Chem Int Ed Engl       Date:  2002-01-04       Impact factor: 15.336

2.  The preparation of 2-alkylbutadienes.

Authors:  C S MARVEL; R L MYERS; J H SAUNDERS
Journal:  J Am Chem Soc       Date:  1948-05       Impact factor: 15.419

3.  Synthesis of compounds related to vitamin A from hydroxymethylene beta-ionone.

Authors:  E M SHANTZ
Journal:  J Am Chem Soc       Date:  1946-12       Impact factor: 15.419

4.  beta-Disubstituted allylic chlorides: substrates for the Cu-catalyzed asymmetric SN2' reaction.

Authors:  Caroline A Falciola; Karine Tissot-Croset; Alexandre Alexakis
Journal:  Angew Chem Int Ed Engl       Date:  2006-09-11       Impact factor: 15.336

5.  Ruthenium-catalyzed two-component addition to form 1,3-dienes: optimization, scope, applications, and mechanism.

Authors:  B M Trost; A B Pinkerton; M Seidel
Journal:  J Am Chem Soc       Date:  2001-12-19       Impact factor: 15.419

6.  Stabilized analogs of thymopentin. 1. 4,5-Ketomethylene pseudopeptides.

Authors:  J I DeGraw; R G Almquist; C K Hiebert; W T Colwell; J Crase; T Hayano; A K Judd; L Dousman; R L Smith; W R Waud; I Uchida
Journal:  J Med Chem       Date:  1997-07-18       Impact factor: 7.446

7.  A Four-Carbon Unit Reagent for the Regiospecific Synthesis of 2-Alkyl-Substituted 1,3-Butadienes.

Authors:  Alan R. Katritzky; Larisa Serdyuk; Dorin Toader; Xiaojing Wang
Journal:  J Org Chem       Date:  1999-03-19       Impact factor: 4.354

8.  Efficient asymmetric synthesis of silanediol precursors from 1,5-dihydrosiloles.

Authors:  Sushmita Sen; Madhusudhan Purushotham; Yingmei Qi; Scott McN Sieburth
Journal:  Org Lett       Date:  2007-10-30       Impact factor: 6.005

9.  Nucleophilicities and carbon basicities of DBU and DBN.

Authors:  M Baidya; Herbert Mayr
Journal:  Chem Commun (Camb)       Date:  2008-03-13       Impact factor: 6.222

10.  1,4-Dichloro- and 1,4-dibromo-2-butenes as substrates for Cu-catalyzed asymmetric allylic substitution.

Authors:  Caroline A Falciola; Alexandre Alexakis
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336
  10 in total

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