李國安   學術特聘教授

描述: D:\data\menu\teacher\teacher\Gon-Ann Lee.jpg

通訊處

辦公室電話︰(02)2905-3563

E-mail

016850@mail.fju.edu.tw

學經歷

台灣師範大學學士(1980)

台灣師範大學研究所碩士(1982)

美國Rice University 博士(1990)

美國The University of Texas. Medical School at Houston 博士後研究員(1989-1990)

輔仁大學化學系副教授(1990-1998)

輔仁大學化學系教授(1998-)
輔仁大學化學系學術特聘教授(2019-)

輔仁大學化學系系主任(1999-2002)(2009-2012)

 

學術專長

有機化學

研究領域

本實驗室的研究範圍主要是有機合成方面，尤其是小環高張力的環丙烯類化合物(cyclopropenes) 之合成及其化學性質的研究。環丙烯因具有很高的環張力— 約54 kcal/ mol— 而引發其特殊的化學性質，這類化合物的重要反應有:
  (1)進行[2+2]環化加成反應而得到三環[3.1.0.02,4]己烷。
  (2)進行開環—閉環反應形成乙烯基甲烯(vinyl carbenes) 類化合物。具有1,2-及1,3-融合雙環結構之環丙烯類化合物的張力又比單純環丙烯大，因此合成這類化合物更具有挑戰性。

由於環丙烯類化合物非常的不安定，在溶液狀態下合成時會有缺點，因此本研究室運用一套特殊裝置-真空氣相-固相反應(Vacuum Gas-Solid Reaction)技術來合成這些高張力的化合物，並用液態氮冷凍住生成物，再對其物性、化性進行研究。

代表著作

1-      Lee, G.-A.,* Lin, H.-C., Lee, H.-Y., Chen, C.-H., Huang, H.-Y., “Ipso Nitration of 2-Halothiophenes with Silver Nitrate, ” Asian J. Org. Chem. 2017, 6, 1733-1736.

2-      Lee, G.-A.,* Shih, Y.-F., Lin, H.-C., Wang, W.-C., Chan, H.-T., Lee, H.-Y., Lee, C.-Y., “Synthesis of Calix[6]thiophenes and Calix[6]furans, ” ChemistrySelect 2020, 5, 8518-8521.

3-      Lin, H.-C., Tsai, R.-T., Wu, H.-P., Lee, H.-Y., Lee, G.-A.,* “Ene di- and trimerization of 1-methyl-2-cyclopropene, ” Tetrahedron, 2016, 72, 184-191.

4-       Lin, C.-N., Huang, C.-Y., Yu, C.-C., Chen, Y.-M., Ke, W.-M.,Wang, G.-J., Lee, G.-A.,* Shieh, M.-H.,* “Iron carbonyl cluster-incorporated Cu(I) NHC complexes in homocoupling of arylboronic acids: an effective [TeFe3(CO)9]2-ligand, ” Dalton Transactions, 2015, 44, 16675-16679.

5-      Lee, G.-A.,* Lee, H.-Y., Chen, W.-C., Lin, Y.-H., “Reaction of,-unsaturated N-benzenesulfonyl Imine – N – [(2E)-3-phenyl-2-propen-1-ylidene]

benzenesulfonamide with Methyllithium, ” J. Chin. Chem. Soc. 2015, 62, 573-576.

6-           Lee, G.-A.,* Lin, H.-C., “Synthesis of an Anti-Bredt Compound, Bicyclo[3.2.2]nona-1,6,8-triene, via the Isomerization of Tricyclo[3.2.1.02,4]nona-2,6-diene, ” Org. Lett. 2014, 16, 5275−5277.

7-       Lee, G.-A.,* Lee, H.-Y., Wang, W.-C., Cherng, C.-H., “Auto de-bromine-coupling reactions of 1-aryl-7-bromocycloheptenes,” Tetrahedron, 2014, 70, 2956-2961.

8-      Lee, G.-A.,* Chan, L.-E., Tsai, R.-T., Chang, K.-C., “Generation and Chemistry of Tricyclo[3.2.1.02,4]oct-2(3)-ene,” Eur. J. Org. Chem. 2012, 2824–2830.

9-       Lee, G.-A.,* Wang, W.-C., Shieh, M., Kuo, T.-S., “A Novel Synthesis of Calix[4]thiophenes and Calix[4]furans,” Chem. Commun. 2010, 46, 5009–5011.

10-   Lee, G.-A.,* Tsai, R.-T., Wang, W.-C., Liu, Y.-T., “The Synthesis and Trapping of 1-Naphthylcyclopropenes,” J. Chin. Chem. Soc. 2010, 57, 800-804.

11-   Lee, G.-A.,* Wang, W.-C., Jiang, S.-F., Chang, C.-Y., Tsai, R.-T., “The Crossed [2+2] Cycloaddition of 1-Phenylcyclopropene and

Bromo-2-phenylcyclopropene,” J. Org. Chem. 2009, 74, 7994–7997.

12-   Lee, G.-A.,* Chen, K.-C., “The General Synthesis and Trapping of 3-Substituted 1-Chlorocyclopropenes,” Org. Lett. 2008, 9, 1843-1845.

13-    Lo, Y.-L., Wang, W.-C., Lee, G.-A., Liu, Y.-H.,* “Bis(u-l-1H-benzimidazole-5,6-dicarboxylato)bis[tetraaquadicobalt(II)] pentahydrate,” Acta Cryst. 2007, 

E63, m2657-m2658.

14-   Chen, K.-C., Wang, W.-C., Chen, M.-Y., Chen, W.-C., Her, M.-C., Lee, G.-A.,* “Regio- and Stereoselectivity of Ene Reactions: The Dimerization of

Bicyclic 1,3-Fused 2-(TrimethylSilyl)cycloprop-1-enes,” Eur. J. Org. Chem. 2007, 953-958.

15-    陳科州, 李國安,* “環丙烯類化合物的合成與化學性質,” Chemistry (J. Chin. Chem. Soc., Taipei) 2006, 64, 73-96.

16-    Lai, Y.-W., Cherng, J.-J., Sheu, W.-S., Lee, G.-A., Shieh, M.,* “Novel Types of Organic S-Fe-CO Complexes: Reaction of [SFe3(CO)9]2- with 

Propargyl Bromide,” Organometallics. 2006, 25, 184-190.

17-    Lee, G.-A.,* Chang, C.-Y., “Novel Ene Trimerization of 1-Phenylcyclopropene,” J. Org, Chem. 2004, 69, 8949-8951.

18-    Lee, G.-A.,* Chang, C.-Y., Cherng, C.-H., Chen, C.-S., Liu, M., “The Synthesis and Chemistry of 1,3-Bridged Polycyclic Cyclopropenes:

8-Oxatricyclo[3.2.1.02,4]octa-2,6-dienes,” J. Chin. Chem. Soc. 2004, 51, 839-845.

19-    Lee, G.-A.,* Cherng, C.-H., Huang, A.-N., Lin, Y.-H., “Synthesis and Chemistry of Tricyclic cyclopropene-tricyclo[3.2.2.02,4]nona-2(4),6-diene,” 

Tetrahedron. 2003, 59, 1539-1545.

20-   Lee, G.-A.,* Lin, Y.-H., Huang, A.-N., Li, Y.-C., Chen, C.-S., Jann, Y.-C., Chen, C.-S., “Isomerization of tricyclo[3.2.2.02,4]nona-2(4),6-diene

to the Anti-Bredt Compound 8-Methylenebicyclo[3.2.1]octa-1,6-diene,” J. Am. Chem. Soc. 1999, 121, 5328-5329.

21-   Lee, G.-A.,* Chen, P.-K., Chen, M.-Y., “The Synthesis and Chemistry of 8-Substituted Bicyclo[5.1.0]oct-1(8)-ene ,” J. Chin. Chem. Soc. 1998, 45, 381-385.

22-   Lee, G.-A.,* Chang, C.-Y., “Novel Tetramerization of 1-Trimethylsilyl-2-Phenylcyclopropene,” Tetrahedron Lett. 1998, 39, 3013-3016.

23-   Lee, G.-A.,* Chen, C.-S., “1-Chloro-3-trimethysilylcyclopropene -- A New Synthesis of 3,3'-Bicyclopropyl,” Tetrahedron Lett. 1997, 38, 8717-8720.

24-   Lee, G.-A.,* Huang, A.-N., Chen, C.-S., Li, Y.-C., Jann, Y.-C., “1,2-Bridged Tricyclic Cyclopropenes:Tricyclo[3.2.1.02,4]octa-2(4),6-diene

and Tricyclo[3.2.1.02,4]oct-2(4)-ene,” J. Org. Chem. 1997, 62, 3355-3359.

25-   Chou, S.-S. P., Lee, G.-A.,* “Improvement of Chemistry Courses for Non-Chemistry Major Undergraduates,” J. Chin. Chem. Soc. 1996, 54, 131-143.

26-   Lee, G.-A.,* Chen, J., Chen, C.-S., Shiau, C.-H., Cherng C.-H., “The Synthesis and Chemistry of 9-Chlorobicyclo[6.1.0]non-1(9)-ene,” J. Chin. Chem. Soc. 

1996, 43, 297-300.

27-   Billups, W.-E.,* Luo, W., Lee, G.-A., Chee, J., “Synthesis and chemistry of Bicyclo[4.1.0]hept-1,6-ene ,” J. Org. Chem. 1996, 61, 764-770.

28-    Lee, G.-A.,* Shiau, C.-S., Chen, C.-S., Chen, J., “Regioselectivity of the Ene Reaction: Dimerization of 8-Chlorobicyclo[5.1.0]oct-1(8)-ene,” 

J. Org. Chem. 1995, 60, 3565-3567.

29-   Billups, W.-E.,* Lee, G.-A., Arney, B.-E., Jr., Whitmire, K.-H., “1,3-Bridged Cyclopropenes,” J. Am. Chem. Soc. 1991, 113, 7980-7984.

30-   Billups, W.-E.,* Haley, M.-M., Lee, G.-A., “Bicyclo[n.1.0]alkenes,” Chem. Rev. 1989, 89, 1147-1159.