The present study investigated the photoreaction of N-(ω-tributylstannylpolyethoxyether)- phthalimides in methanol solution. The results obtained were compared with that reported in previous studies. It is shown that photoinduced single electron transfer cyclization reaction proceeds by destannation at a higher efficiency than the cyclization reaction by desilylation, which suggests a feasibility of increasing the selectivity and productivity of single-electron cyclization reaction through improving the cleavability of the leaving group. The structure of all the new compounds and final cyclic compounds were characterized by using ¹H NMR,¹³C NMR, HRMS technology.

Key words: photoinduced single electron transfer, tributylstannyl, trimethylsilyl, leaving group, cyclocompound