Synthesis of 1,2-Diphospholides Using a Main Group "superbase"
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Peer-reviewed
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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.
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3402 Inorganic Chemistry, 3405 Organic Chemistry, 34 Chemical Sciences
Journal Title
Organometallics
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Journal ISSN
0276-7333
1520-6041
1520-6041
Volume Title
37
Publisher
American Chemical Society (ACS)
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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.).