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Solvent reduced wittig olefination reactions with halo containing conjugated phosphoranes

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Thiemann T., Tanaka Y., Ideta K., Mataka S.
Open Chemistry
|
2006
|
vol. 4
|
issue 3
403-427
EN
The Wittig reaction of carbaldehydes with alkoxycarbonylhalomethylidenetriphenylphosphoranes can be performed with ease in solventless systems. The analogous reaction of carbaldehydes with acylhalomethylidenetriphenylphosphoranes requires a small amount of solvent, such as chloroform, in order for the reaction to proceed. The products of the reaction are versatile precursors for further transformations, such as the Suzuki-Miyaura cross-coupling reaction.
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Heteroareno-annelated estranes by triene cyclization

100%
Watanabe M., Matsumoto T., Mataka S., Thiemann T.
Open Chemistry
|
2006
|
vol. 4
|
issue 3
375-402
EN
17-Thienyl-and 17-benzo[b]thienyl-3-hydroxyestra-1,3,5(10),16-tetraenes were synthesized by either sequential or one-pot Suzuki cross-coupling and Wittig olefination reactions. At 160 °C, heteroaryl substituted steroids were observed to undergo thermal intramolecular cyclization to produce E-ring heteroareno-annelated estranes.
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