An Easy Access to Stereodefined 2-Pentenyltins by Partial Hydrogenation of 2,4-Pentadienyltins with Diazene

Tributyl-(2-pentenyl)tins were readily prepared in high yield by hydrogenation of tributyl-(2,4-pentadienyl)tins with diazene generated from 2,4,6-triisopropylbenzenesulfonohydrazide. The terminal double bond was selectively hydrogenated in the conjugated diene system. The stereochemistry of the internal double bond was completely retained.

[1]  Y. Naruta,et al.  Versatile roles of Lewis acids in the reactions of allylic tin compounds , 1993 .

[2]  A. Takuwa,et al.  α-Regioselective and stereospecific addition of allylic tins to aldehydes via photoinduced electron transfer , 1993 .

[3]  T. Hamasaki,et al.  A highly effective one-pot bicycloannulation methodology for the synthesis of berban and yohimban systems based on organotin-mediated three-component coupling (N-acylative pentadienylation of C:N bonds) , 1993 .

[4]  Y. Naruta,et al.  Highly selective trapping of unsymmetrical pentadienyl anions by silicon and tin electrophiles. Marked contrast between kinetic and thermodynamic control of product composition , 1991 .

[5]  Yoshinori Yamamoto,et al.  Acyclic stereocontrol via allylic organometallic compounds , 1987 .

[6]  M. Paz-Sandoval,et al.  Diene and dienyl complexes of transition elements: IV1. η5-Pentadienyltricarbonylrhenium , 1981 .

[7]  A. Nakamura,et al.  Chemistry of Dienyl Anions. IV. Geometry of Pentadienyl Anions in Solution and in the Solid State Determined by Regioselective Trimethylsilylation and NMR , 1981 .

[8]  K. Maruyama,et al.  A new procedure for the stereoselective synthesis of (Z)-2-alkenylsilanes and -tins and their application to erythro-selective synthesis of .beta.-alkyl alcohol derivatives , 1980 .

[9]  P. Cadiot,et al.  Derives β-alcenyles des metaux de la colonne IVB : I. Action des metalates de lithium, de type R3MLi, sur les chlorures de crotyle cis et trans et sur le chloro-3 butene-1 , 1976 .

[10]  C. Reese,et al.  2,4,6-Tri-isopropylbenzenesulphonyl hydrazide: A convenient source of di-imide , 1976 .

[11]  K. Mori,et al.  Synthesis of compounds with juvenile hormone activity—XI , 1972 .

[12]  C. E. Miller,et al.  Hydrogenation with diimide , 1965 .