A selective Cu(II)/Fe(III)-mediated hydrogenation of steroidal haloalkenes in the presence of hydrazine

Tetrahedron Letters

Volumn 44, Issue 7, 2003, Pages 1351-1354

  Chang, Kai Hsuan ^a   Jenkins, Malikah N ^b   Wu, Hsin Ru ^a   Li, Wen Shan ^a  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

^b PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANDROGEN RECEPTOR; ANTIESTROGEN; COPPER COMPLEX; HYDRAZINE; STEROID;

ARTICLE; COMPLEX FORMATION; DEHALOGENATION; HYDROGENATION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037429070     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02875-7     Document Type: Article

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26. The reaction time can totally be shortened to 24 h or less when hydrazine hydrate was frequently added into solution to facilatate the reaction.
27. +, 353.0752; found, 353.0758.
28. The controversy was also reported by Nelson, D. J., et al. This shows that hydrogen reactions are not exclusively controlled by both electronic and steric effects in the present conditions. Torsional strain and bond angle bending strain may contribute to the observed reactivity differences.
29. It should be noted that hydrogenation of the double bond is not caused by hydrazine itself but by a oxidation product, diimide, of hydrazine.