Abstract
Reactions of allylstannanes (or allenylstannanes) with aldehyde monothioacetals proceed in two different ways as shown in Scheme 1 to afford 4-methoxy-1-alkenes (or alkynes) in the presence of BF3OEt2, or alternatively 4-phenylthio-1-alkenes (or alkynes) in the presence of TiCl4. The required monothioacetals are prepared from RX and LiCH(SPh)OMe. In effect, therefore, CH2(SPh)OMe provides H-C-OMe or H-C-SPh type carbene synthon connecting R+ and C=C-CH2 − or C≡C-CH2 − synthons.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsAuthor information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1989 Kluwer Academic Publishers
About this chapter
Cite this chapter
Sato, T., Otera, J., Nozaki, H. (1989). Carbene Synthons in Monothioacetal Reactions. In: Schubert, U. (eds) Advances in Metal Carbene Chemistry. NATO ASI Series, vol 269. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-2317-1_42
Download citation
DOI: https://doi.org/10.1007/978-94-009-2317-1_42
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-010-7541-1
Online ISBN: 978-94-009-2317-1
eBook Packages: Springer Book Archive