Issue 5, 2020

Diels–Alder reactions of 1-phosphabutadienes: a highly selective route to P[double bond, length as m-dash]C-substituted phosphacyclohexenes

Abstract

Kinetically stabilized 1-phosphahaloprenes (2-halo-1-phosphabutadienes) as well as 1-phosphaisoprene undergo a hitherto unknown phospha-Diels–Alder dimerization of the P[double bond, length as m-dash]C–C[double bond, length as m-dash]C units upon heating. The [4+2] cyclodimerization is highly stereo- and regio-selective. The phosphaalkene-substituted phosphacyclohexene product is an unprecedented P(sp2),P(sp3) ligand that is of interest in polymer/materials science and catalysis.

Graphical abstract: Diels–Alder reactions of 1-phosphabutadienes: a highly selective route to P [[double bond, length as m-dash]] C-substituted phosphacyclohexenes

Supplementary files

Article information

Article type
Communication
Submitted
19 Nov 2019
Accepted
05 Dec 2019
First published
05 Dec 2019

Chem. Commun., 2020,56, 774-777

Author version available

Diels–Alder reactions of 1-phosphabutadienes: a highly selective route to P[double bond, length as m-dash]C-substituted phosphacyclohexenes

K. Ohtsuki, H. T. G. Walsgrove, Y. Hayashi, S. Kawauchi, B. O. Patrick, D. P. Gates and S. Ito, Chem. Commun., 2020, 56, 774 DOI: 10.1039/C9CC08997G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements