Two novel intramolecularly electronical donor-acceptor systemes N-[2-(2-tributylstannylmethyl-sulfenyl)-ethyl]phthalimide (1a) and N-(3-tributylstanylpropyl)maleimide (1b), were synthesized, and their photoinduced single electron transfer (SET) reactions in MeOH, CH3CN-30% H2O and pure CH3CN were carried out, respectively. Compound 1a occurred intramolecular SET to provide cyclic amidol 2 with highly yield and high regioselectivity. Compound 1b occurred intramolecular single electron transfer (SET) to provide cyclic amidol 3 with small amount of photoinduced [2+2] dimerization product 4. Structures of all new compounds were characterized by MS (FAB) and NMR data.
Jin Yingxue
,
Wang Xin
,
Qu Fengyu
,
Tan Guanghui
,
Yue Qunfeng
. Photoinduced Single Electron Transfer Cyclization Reactions of N-(Trimethylstannyl terminated substituent group)imide[J]. Chinese Journal of Organic Chemistry, 2012
, 32(12)
: 2363
-2367
.
DOI: 10.6023/cjoc201205027
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