Hydrophosphination of Vinyl Sulfides and Vinyl Selenides: First Examples

Boris A.  Trofimov; Nina K.  Gusarova; Svetlana F.  Malysheva; Nina I.  Ivanova; Boris G.  Sukhov; Natal’ya A.  Belogorlova; Vladimir A.  Kuimov

doi:10.1055/s-2002-34852

PAPER

Hydrophosphination of Vinyl Sulfides and Vinyl Selenides: First Examples

Boris A. Trofimov, Nina K. Gusarova*, Svetlana F. Malysheva, Nina I. Ivanova, Boris G. Sukhov, Natal’ya A. Belogorlova, Vladimir A. Kuimov
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Favorsky Street 1, 664033 Irkutsk, Russia
Fax: +7(3952)396046; e-Mail: gusarova@irioch.irk.ru;

Abstract

All articles of this category

Abstract

The first examples of the hydrophosphination of alkyl vinyl sulfides and selenides are described. The reaction of secondary phosphines (R¹)₂PH 1-3 with vinyl chalcogenides CH₂=CHXR² 4-9 proceeds readily under radical initiation to give in anti-Markovnikov mode regiospecifically the corresponding organylchalcogenophosphines (R¹)₂PCH₂CH₂XR² 10a-h in high yields.

Key words

phosphines - sulfur - selenium - phosphorus - addition reactions - radicals

Full Text

References

1a Trofimov BA. Arbuzova SN. Gusarova NK. Russ. Chem. Rev. 1999, 68: 215

1b Terence NM. Kerstin H. J. Organometal. Chem. 1991, 409: 163

1c Wolfsberger W. Chem. Ztg. 1988, 112: 53

1d Malysheva SF. Gusarova NK. Belogorlova NA. Nikitin MV. Gendin DV. Trofimov BA. Zh. Obshch. Khim. 1997, 67: 63

2a Gusarova NK. Malysheva SF. Arbuzova SN. Trofimov BA. Russ. Chem. Bull. 1998, 47: 1645

2b Gusarova NK. Brandsma L. Malysheva SF. Arbuzova SN. Trofimov BA. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 111: 174

2c Khachatryan RA. Sayadyan SV. Grigoryan NYu. Indzhikyan MG. Zh. Obshch. Khim. 1988, 58: 2472 ; Chem. Abstr. 1989, 111, 134304w

3a Wicht DK. Kovacik I. Glueck DS. Organometallics 1999, 18: 5141

3b Wicht DK. Kourkine IV. Kovacik I. Glueck DS. Organometallics 1999, 18: 5381

3c Kovacik I. Wicht DK. Grewal NS. Glueck DS. Organometallics 2000, 19: 950

4 Trofimov BA. Sulfur Rep. 1992, 207

5 Trofimov BA. Gusarova NK. Brandsma L. Main Group Chem. News 1996, 4: 18

6a Slone CS. Weinberger DA. Mirkin CA. Prog. Inorg. Chem. 1999, 48: 233

6b Liek C. Machnitzki R. Nickel T. Schenk S. Tepper M. Stelzer O. Z. Naturforsch. 1999, 54b: 1532

6c Hingst M. Tepper M. Stelzer O. Eur. J. Inorg. Chem. 1998, 73

6d Herd O. Hebter A. Hingst M. Machnitzki R. Tepper M. Stelzer O. Catal. Today 1998, 42: 413

6e Brauer DJ. Kottsieper KW. Nickel T. Sheldrick WS. Eur. J. Inorg. Chem. 2001, 1251

6f Bader A. Linder E. Coord. Chem. Rev. 1991, 108: 27

7a Minami T. Okauchi T. Matsuki H. Nakamura M. Ichikawa J. Ishida M. J. Org. Chem. 1996, 61: 8132

7b Minami T. Okauchi T. Kouno R. Synthesis 2001, 349

8 Arbuzova SN. Brandsma L. Gusarova NK. Trofimov BA. Recl. Trav. Chim. Pays-Bas 1994, 113: 575

9 Trofimov BA. Brandsma L. Arbuzova SN. Malysheva SF. Gusarova NK. Tetrahedron Lett. 1994, 35: 7647

10 Gusarova NK. Trofimov BA. Malysheva SF. Shaikhudinova SI. Belogorlova NA. Arbuzova SN. Nepomnyashchikh KV. Dmitriev VI. Zh. Obshch. Khim. 1997, 67: 70 ; Chem. Abstr. 1998, 128, 257494g

11 Gusarova NK. Potapov VA. Amosova SV. Trofimov BA. Zh. Org. Khim. 1983, 19: 2477 ; Chem. Abstr. 1984, 101, 6574r