N-Bu3SnH

A C N 1,2-aryl rearrangement was observed when alkyl azides were treated with n-Bu3SnH, proceeding via an C—N —SnBu3 species to give an imine. ... 

Alkoxy (R0 ) radicals react at near diffusion controlled rates with trialkyl phosphites to give phosphoranyl radicals [ROP(OR )3] that typically undergo very fast -scission to generate alkyl radicals (R ) and phosphates [OP(OR )3]. In a mechanistic study, trimethyl phosphite, P(OMe)3, has been used as an efficient and selective trap in oxiranylcarbinyl radical systems formed from haloepoxides under thermal AIBN/n-Bu3SnH conditions at about 80 °C (Scheme 27) [64]. The formation of alkenes resulting from the capture of allyloxy radicals by P(OMe)3 fulfils a prior prediction that, under conditions close to kinetic control, products of C-0 cleavage (path a. Scheme 27), not just those of C-C cleavage (path b. Scheme 27) may result. 

Scheme 64. Synthesis of raddeanamine (360). Reagents a, MeMgl b, MCPBA c, hv, MeOH d, NaBH4 or LiAl(OBu )3 e, HCHO f, SOCI2 g, n-Bu3SnH h, NaBH3CN i, A j, MeLi.

Reagents and conditions i, p-TSA, heat ii, n-Bu3SnH, AIBN, heat iii, TiCI4 iv, Me2AICI... 

The lifetimes of the transients in CH3CN were independent of O2 or n-Bu3SnH concentrations. These observations rule out the possibility that the transient spectra are due to triplets or radicals. ... 

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