Diethyl [Nitro(diazo)methyl]phosphonate:
Synthesis and Reactivity towards Alkenes

Andrey V. Chemagin; Nikolai V. Yashin; Yuri K. Grishin; Tamara S. Kuznetsova; Nikolai S. Zefirov

doi:10.1055/s-0029-1217103

PAPER

Diethyl [Nitro(diazo)methyl]phosphonate: Synthesis and Reactivity towards Alkenes

Andrey V. Chemagin^a, Nikolai V. Yashin*^a,b, Yuri K. Grishin^a, Tamara S. Kuznetsova^a,b, Nikolai S. Zefirov^a,b
^a Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation
Fax: +7(495)9393969; e-Mail: yashin-n@org.chem.msu.ru;
^b IPhAC RAS, Severnyi Proezd, 1, Chernogolovka, Moscow Region, 142432, Russian Federation

Abstract

All articles of this category

Abstract

A novel and convenient synthesis of diethyl [nitro(diazo)methyl]phosphonate and its reactions with various alkenes are described. The reactivity of diethyl [nitro(diazo)methyl]phosphonate is shown to be dependent on the structure of the alkene. A number of cyclopropyl α-nitrophosphonates were obtained.

Key words

diazo compounds - phosphonates - alkenes - cyclopropanation - carbenes

Full Text

References

<A NAME="RZ18809SS-1">1</A> Sheridan RP. J. Chem. Inf. Comput. Sci. 2002, 42: 103

For comprehensive reviews, see:

<A NAME="RZ18809SS-2A">2a</A> Ordóñez M. Rojas-Cabrera H. Cativiela C. Tetrahedron 2009, 65: 17

<A NAME="RZ18809SS-2B">2b</A> Kafarski B. Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63: 193

<A NAME="RZ18809SS-2C">2c</A> Wolfenden R. Annu. Rev. Biophys. Bioeng. 1976, 5: 271

<A NAME="RZ18809SS-3">3</A> For a recent review, see: Brackmann F. de Meijere A. Chem. Rev. 2007, 107: 4493

<A NAME="RZ18809SS-4A">4a</A> Erion MD. Walsh CT. Biochemistry 1987, 26: 3417

<A NAME="RZ18809SS-4B">4b</A> Groth U. Lehmann L. Richter L. Schöllkopf U. Liebigs Ann. Chem. 1993, 427

<A NAME="RZ18809SS-4C">4c</A> Yamazaki S. Takada T. Moriguchi Y. Yamabe S. J. Org. Chem. 1998, 63: 5919

<A NAME="RZ18809SS-4D">4d</A> Fadel A. J. Org. Chem. 1999, 64: 4953

<A NAME="RZ18809SS-4E">4e</A> Tesson N. Dorigneux B. Fadel A. Tetrahedron: Asymmetry 2002, 13: 2267

<A NAME="RZ18809SS-5A">5a</A> Yashin NV. Averina EB. Gerdov SM. Kuznetsova TS. Zefirov NS. Tetrahedron Lett. 2003, 44: 8241

<A NAME="RZ18809SS-5B">5b</A> Yashin NV. Averina EB. Grishin YuK. Kuznetsova TS. Zefirov NS. Synthesis 2006, 279

<A NAME="RZ18809SS-6A">6a</A> Averina EB. Yashin NV. Kuznetsova TS. Zefirov NS. Vestn. Mosk. Univer., Ser. 2: Khim. 2002, 43: 246 ; Chem. Abstr. 2002, 138, 254854

<A NAME="RZ18809SS-6B">6b</A> Averina EB. Yashin NV. Shvorina EB. Grishin YuK. Kuznetsova TS. Vestn. Mosk. Univer., Ser. 2: Khim. 2005, 46: 314 ; Chem. Abstr. 2005, 145, 145989

<A NAME="RZ18809SS-6C">6c</A> Yashin NV. Averina EB. Grishin YuK. Kuznetsova TS. Zefirov NS. Synthesis 2006, 880

<A NAME="RZ18809SS-7A">7a</A> Matveeva ED. Podrugina TA. Tishkovskaja EV. Tomilova LG. Zefirov NS. Synlett 2003, 2321

<A NAME="RZ18809SS-7B">7b</A> Zefirov NS. Matveeva ED. ARKIVOC 2008, (i): 1

<A NAME="RZ18809SS-7C">7c</A> Yashin NV. Villemson EV. Chemagin AV. Averina EB. Kabachnik MM. Kuznetsova TS. Synthesis 2008, 464

<A NAME="RZ18809SS-8">8</A> Regitz M. Weber B. Eckstein U. Liebigs Ann. Chem. 1979, 1002

<A NAME="RZ18809SS-9A">9a</A> Sifniades S. J. Org. Chem. 1975, 40: 3562

<A NAME="RZ18809SS-9B">9b</A> Neimysheva AA. Muratov SS. Smirnov EV. Solntseva LM. Zh. Obshch. Khim. 1976, 46: 940 ; Chem. Abstr. 1976, 85, 712

<A NAME="RZ18809SS-9C">9c</A> Takeuchi Y. Ogura H. Kanada A. Koizumi T. J. Org. Chem. 1992, 57: 2196

<A NAME="RZ18809SS-10">10</A> Charette AB. Wurz RP. Ollevier T. J. Org. Chem. 2000, 65: 9252

<A NAME="RZ18809SS-11A">11a</A> Charette AB. Wurz RP. J. Mol. Catal. A: Chem. 2003, 196: 83

<A NAME="RZ18809SS-11B">11b</A> Titanyuk ID. Beletskaya IP. Peregudov AS. Osipov SN. J. Fluorine Chem. 2007, 128: 723

<A NAME="RZ18809SS-12">12</A> Charette AB. Wurz RP. Ollevier T. Helv. Chim. Acta 2002, 85: 4468

<A NAME="RZ18809SS-13">13</A> Perrin DD. Armarego WLF. Purification of Laboratory Chemicals Pergamon; Oxford: 1966. p.362

<A NAME="RZ18809SS-14">14</A> Calogeropoulou T. Hammond GB. Wiemer DF. J. Org. Chem. 1987, 52: 4185

<A NAME="RZ18809SS-15">15</A> Binger P. Brinkmann A. Wedemann P. Synthesis 2002, 1344

<A NAME="RZ18809SS-16">16</A> Zefirov NS. Kozhushkov SI. Kuznetsova TS. Kokoreva OV. Lukin KA. Trach SS. Ugrak BI. J. Am. Chem. Soc. 1990, 112: 7702

<A NAME="RZ18809SS-17">17</A> Sternberg E. Binger P. Tetrahedron Lett. 1985, 26: 301

<A NAME="RZ18809SS-18">18</A> Cripps HN. Williams JK. Sharkey WH. J. Am. Chem. Soc. 1959, 81: 2723

<A NAME="RZ18809SS-19">19</A> Beckhaus H.-D. Ruechardt C. Kozhushkov SI. Belov VN. Verevkin SP. de Meijere A. J. Am. Chem. Soc. 1995, 117: 11854

<A NAME="RZ18809SS-20">20</A> Christol H. Cristau H.-J. Soleiman M. Synthesis 1975, 736

<A NAME="RZ18809SS-21">21</A> Neimysheva AA. Muratov SS. Smirnov EV. Solntseva LM. Zh. Obshch. Khim. 1976, 46: 940 ; Chem. Abstr. 1976, 85, 712