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Issue 5, 2020
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Diels–Alder reactions of 1-phosphabutadienes: a highly selective route to P[double bond, length as m-dash]C-substituted phosphacyclohexenes

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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

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Article information


Submitted
19 Nov 2019
Accepted
05 Dec 2019
First published
05 Dec 2019

Chem. Commun., 2020,56, 774-777
Article type
Communication

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

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