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Abstract:

Tetraethyl vinylidenebisphosphonate is a versatile synthetic intermediate that allows access to a variety of highly functionalized compounds bearing the bisphosphonic moiety. As an electron-deficient alkene, this compound is able to undergo conjugate addition with a variety of reagents including strong nucleophiles, such as organometallic reagents and enolates, as well as very mild nucleophiles, such as amines, mercaptans and alcohols. The title compound also possesses the ability to behave as a dipolarophile or dienophile in 1,3-dipolar cycloadditions or Diels-Alder reactions, giving rise to five- or six-membered rings containing the bisphosphonic unit. In summary, tetraethyl vinylidenebisphosphonate is a very useful synthon to have at hand for straightforward syntheses of bisphosphonate derivatives of diverse structures. This bisphosphonate moiety has proven to be very important to impart important pharmacological action. 1 Introduction 2 General Reactivity 3 Michael Addition Reactions 3.1 Reaction with Organometallic Reagents 3.2 Reaction with Mercaptans and Amines 3.3 Reaction with Phosphorus-Containing Nucleophiles 3.4 Epoxidation, Loss of a Phosphonate Unit and Rearrangement Reactions 3.5 Michael Reactions with Enolates 4. Cycloaddition Reactions 4.1 Diels-Alder Reactions 4.2 1,3-Dipolar Cycloadditions 4.2.1 Reaction with Diazo Compounds 4.2.2 Reaction with Nitrones 4.2.3 Reaction with Nitrile Oxides 4.2.4 Grigg Azomethine Ylide Cyclizations 4.2.5 Reaction with Azides 5 Concluding Remarks. © Georg Thieme Verlag Stuttgart, New York.

Registro:

Documento: Artículo
Título:Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates
Autor:Rodriguez, J.B.
Filiación:Departamento de Química Orgánica and UMYMFOR (CONICET-FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, C1428EHA, Buenos Aires, Argentina
Palabras clave:1 3-dipolar cycloadditions; bisphosphonates; Michael additions; tetraethyl vinylidene bisphosphonate; Amines; Chemical compounds; Cycloaddition; Nitrogen oxides; Nucleophiles; Olefins; Organometallics; 1 ,3-dipolar cycloadditions; Bisphosphonates; Cycloadditions; Functionalized compounds; Michael addition reactions; Michael additions; Rearrangement reactions; Synthetic intermediates; Addition reactions; amine; azide; azomethine ylide; bisphosphonic acid derivative; nitrile oxide; nitrone derivative; phosphonic acid derivative; phosphorus; tetraethyl vinylidenebisphosphonate; thiol; unclassified drug; chemical structure; concentration (parameters); cyclization; cycloaddition; enantioselectivity; epoxidation; Michael addition; oxidation reduction reaction; physical chemistry; review; stereochemistry; structure analysis
Año:2014
Volumen:46
Número:9
Página de inicio:1129
Página de fin:1142
DOI: http://dx.doi.org/10.1055/s-0033-1340952
Título revista:Synthesis (Germany)
Título revista abreviado:Synthesis
ISSN:00397881
CODEN:SYNTB
CAS:azide, 12596-60-0, 14343-69-2; azomethine ylide, 107081-71-0, 1761-67-7, 176903-89-2; phosphorus, 7723-14-0
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v46_n9_p1129_Rodriguez

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Citas:

---------- APA ----------
(2014) . Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates. Synthesis (Germany), 46(9), 1129-1142.
http://dx.doi.org/10.1055/s-0033-1340952
---------- CHICAGO ----------
Rodriguez, J.B. "Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates" . Synthesis (Germany) 46, no. 9 (2014) : 1129-1142.
http://dx.doi.org/10.1055/s-0033-1340952
---------- MLA ----------
Rodriguez, J.B. "Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates" . Synthesis (Germany), vol. 46, no. 9, 2014, pp. 1129-1142.
http://dx.doi.org/10.1055/s-0033-1340952
---------- VANCOUVER ----------
Rodriguez, J.B. Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates. Synthesis. 2014;46(9):1129-1142.
http://dx.doi.org/10.1055/s-0033-1340952