合成了两种新的分子内给受电子体系N-[2-(2-三丁基锡甲硫基)乙基]邻苯二甲酰亚胺(1a)和N-(3-三丁基锡丙基)马来酰亚胺(1b), 并在甲醇、乙腈-30%水、乙腈中进行了光诱导单电子转移反应. 化合物1a在光诱导下发生分子内单电子转移反应, 以很高的产率和区域选择性生成环胺醇2. 化合物1b在光诱导下发生分子内单电子转移反应生成环胺醇3, 同时有[2+2]环加成副反应产物4生成. 以上所有新化合物的结构经质谱和核磁共振谱验证.
金英学
,
王欣
,
曲凤玉
,
谭广慧
,
岳群峰
. N-(末端三丁基锡取代基)酰亚胺的光诱导单电子转移成环反应[J]. 有机化学, 2012
, 32(12)
: 2363
-2367
.
DOI: 10.6023/cjoc201205027
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.
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