A convenient synthesis of specifically substituted conjugated dienes via organocopper(I) induced SN2′ reactions. An attractive route to myrcene
- 1 January 1980
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 99 (11) , 340-343
- https://doi.org/10.1002/recl.19800991104
Abstract
The paper describes the preparation of a number of symmetrically substituted 1,3‐dienes H2C=C(R)‐C(R)=CH2 (3a‐d) as well as non‐symmetrically substituted 1,3‐dienes H2C=C(R1)‐C(R)=CR2R3 (3e‐i, R ≠ R1) by means of organocuprate induced SN2′ reactions in the esters X‐CH2‐C≡C‐CH2‐X (1, X = MeS(O)O or ToS‐O) and MeS(O)‐O‐CH2‐C(R1)=C=CR2R3 (4) respectively. An attractive application of the method is the easy preparation of the natural compound myrcene from 4 in which R1, R2 and R3 are hydrogen. A mechanistic rational for the reactions is discussed.Keywords
This publication has 10 references indexed in Scilit:
- Organocuprate induced allylic versus propargylic 1,3‐substitution in sulfinates and sulfonates derived from 3‐hydroxy‐1‐penten‐4‐ynes. Improved synthesis of a precursor for the presumed sex attractant of Acanthoscelides obtectusRecueil des Travaux Chimiques des Pays-Bas, 1979
- A New and General Route to 1-Trimethylsilyl-1,2-alkadienesSynthesis, 1979
- An easy route to some α- and β- allenic alcohols via organocopper(I) induced 1,3- substitution in propargylic methanesulfinates .Tetrahedron Letters, 1979
- A new synthesis of allenic hydrocarbons from tertiary 2‐propynyl sulfinates and organocopper(I) compounds. Evidence for a syn‐l,3‐substitution pattern in the steroid seriesRecueil des Travaux Chimiques des Pays-Bas, 1978
- A New, Stereospecific Synthesis of 2-Alkenenitriles from 2-Alkynenitriles and OrganocupratesSynthesis, 1978
- Stereospecific formation of conjugated dienes from 3-alken-1-ynes and organocuprates. Application in the systhesis of myrcene.Tetrahedron Letters, 1977
- Structure of lithium dimethylcuprate and mechanism of the Corey-Posner reactionJournal of the American Chemical Society, 1976
- The Organic Chemistry of CopperPublished by Elsevier ,1974
- Estimation of the chemical shifts of olefinic protons using additive increments—IITetrahedron, 1969
- Hard and soft acids and bases, HSAB, part 1: Fundamental principlesJournal of Chemical Education, 1968