Synthesis of 1,2-Diphospholides Using a Main Group "superbase"
Authors
Dixon, LSH
Hanf, S
Waters, JE
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Abstract
The synthesis of a range of 1,2-diphospholides can be achieved by a one-pot procedure involving the reactions of aro-matic primary phosphines bearing ortho-CH2 substituents with the superbase mixture of nBuLi/Sb(NMe2)3 in the pres-ence of the Lewis base donor TMEDA (Me2NCH2CH2NMe2). The synthesis of the parent benzo-1,2-diphospholide, and the substituted derivatives 4-methoxybenzo-1,2-diphospholide, 9-methylbenzo-1,2-diphospholide and naphtho-1,2-diphospholide are reported from readily prepared primary phosphines. Bulk synthesis of the potassium salt of the previ-ously reported 4,6-dimethylbenzo-1,2-diphospholide anion using this route provides a convenient starting material for reactivity studies.
Publication Date
2018
Online Publication Date
2018-09-17
Acceptance Date
2018-09-04
Keywords
3402 Inorganic Chemistry, 3405 Organic Chemistry, 34 Chemical Sciences
Journal Title
Organometallics
Journal ISSN
0276-7333
1520-6041
1520-6041
Volume Title
37
Publisher
American Chemical Society (ACS)
Sponsorship
The Cambridge Commonwealth European and International Trust
Gonville and Caius College Cambridge
The Studienstiftung des deutschen Volkes, Fonds of the Chemical Industry
Selwyn College Cambridge (Walters-Kundert Studentship, J.E.W.).