Additions of malononitrile radicals to alkenes under mild conditions using 2,2'azobis-(2,4-dimethyl-4-methoxyvaleronitrile) (V-70) as an initiator

Tetrahedron Letters

Volumn 38, Issue 20, 1997, Pages 3549-3552

  Kita, Yasuyuki ^a   Sano, Atsunori ^b   Yamaguchi, Takahiro ^b   Oka, Masahisa ^b   Gotanda, Kentoku ^a   Matsugi, Masato ^a  

^a OSAKA UNIVERSITY   (Japan)

^b FUJIFILM Wako Pure Chemical Corporation   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NITRILE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030923305     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00700-4     Document Type: Article

References (22)

1. 2,2′-Azobis-(2,4-dimethyl-4-methoxyvaleronitrile) is commercially available from Wako Pure Chemical Ind. Ltd., (Japan) and the abbreviation in parentheses is its trade name. This compound is a mixture of diastereomeric isomers whose melting point are 58 °C and 107 °C and should be stored below-10 °C to prevent any decomposition. V-70 is stable in a refrigerator for a few months and the pure V-70 can be easily obtained by the following procedure: V-70 (10.0 g, ca. 90% content) was added to dry acetone (20ml) at -10 °C under stirring. The heterogeneous solution was stirred for 30 min at -10 °C. Collecting the crystalline precipitates afforded 6.2g of pure V-70 (62%, >99% content).
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11. 2b): AIBN, 65 °C; V-70, 30 °C.
12. 2 (10ml) was stirred at room temperature in the dark. After 12hr, the mixture was concentrated in vacuo. The residue was recrystallized from IPA (10ml) to give 3a in 79% yield.
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