Title page
Contents
Abstract in Korean 6
Part I Introduction 7
Part II Results and discussion 9
II-1. Synthesis and crystal structure of 5-(4-bromophenyl)-2-methyl - 3-methylsulfanyl-1-benzofuran (1) 9
II-2. Synthesis and crystal structure of 5-(4-bromophenyl)-3-methyl-sulfanyl-2-phenyl-1-benzofuran (2) 12
II-3. Synthesis and crystal structure of 2-methyl-1-(methylsulfinyl) naphtho[2,1-b]furan (3) 15
II-4. Synthesis and crystal structure of 2-methyl-3-(methylsulfinyl) naphtho[1,2-b]furan (4) 18
Part III Experimental 21
III-1. Instruments and reagents 21
III-2. The compound (1) 21
III-3. The compound (2) 24
III-4. The compound (3) 26
III-5. The compound (4) 28
Part IV Conclusions 30
Appendix 31
References 55
ABSTRACT 57
감사의 말씀 59
Table 1. Crystal data and structure refinement for compound (1). 23
Table 2. Crystal data and structure refinement for (2). 25
Table 3. Crystal data and structure refinement for (3). 27
Table 4. Crystal data and structure refinement for (4). 29
Table 5. Atomic coordinates (x 10⁴) and equivalent isotropic displacement parameters (A² x 10³) for (1). U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. 31
Table 6. Bond lengths [Å] and angles [deg] for (1). 32
Table 7. Anisotropic displacement parameters (A² x 10³) for (1). The anisotropic displacement factor exponent takes the form: -2 π² [h² a*² U11 + ... + 2 h k b* U12](이미지참조) 35
Table 8. Hydrogen coordinates (x 10⁴) and isotropic displacement parameters (A² x 10³) for (1). 36
Table 9. Atomic coordinates (x 10⁴) and equivalent isotropic displacement parameters (A² x 10³) for (2). U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. 37
Table 10. Bond lengths [Å] and angles [deg] for (2). 38
Table 11. Anisotropic displacement parameters (A² x 10³) for (2). The anisotropic displacement factor exponent takes the form: -2 π² [h² a*² U11 + ... + h k a* b * U12](이미지참조) 42
Table 12. Hydrogen coordinates (x 10⁴) and isotropic displacement parameters (A² x 10³) for (2). 43
Table 13. Bond lengths [Å] and angles [deg] for (3). 44
Table 14. Anisotropic displacement parameters (A² x 10³) for (3). The anisotropic displacement factor exponent takes the form: -2 π² [h² a*² U11 + ... + 2 h k a* b * U12](이미지참조) 47
Table 15. Hydrogen coordinates (x 10⁴) and isotropic displacement parameters (A² x 10³) for (3). 48
Table 16. Atomic coordinates (x 10⁴) and equivalent isotropic displacement parameters (A² x 10³) for (4). U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. 49
Table 17. Bond lengths [Å] and angles [deg] for (4). 50
Table 18. Anisotropic displacement parameters (A² x 10³) for (4). The anisotropic displacement factor exponent takes the form: -2 π² [h² a*² U11 + ... + 2 h k a* b * U12](이미지참조) 53
Table 19. Hydrogen coordinates (x 10⁴) and isotropic displacement parameters (A² x 10³) for (4). 54
Figure 1. The molecular structure of (1), with 30% probability displacement ellipsoids. 10
Figure 2. A partial packing diagram for (1), with C-H…π interactions shown as dotted lines. Cg is the centroid of the furan ring. Symmetry codes: (i) 2-x, y-½, ½-z; (ii) 2-x, y+½, ½-z.] 11
Figure 3. The molecular structure of (2), with 30% probability displacement ellipsoids. 13
Figure 4. A partial packing diagram for (2), with C9-H9…Oi hydrogen bond and the C2ii-H2ii…Cg π interactions drawn as dotted lines. Cg is the centroid of C7-C10/ C13-C14 benzene ring.[Symmetry codes: (i) -x, -y, -z; (ii) x-1, y, z.](이미지참조) 14
Figure 5. The molecular structure of (3), with 30% probability displacement ellipsoids. 16
Figure 6. The π-π and C-H…π interactions in (3). Cg denotes the centroid of each ring [Symmetry codes: (i) 1-x, 2-y, -z; (ii) -x, 2-y, -z.] 17
Figure 7. The molecular structure of (4), showing 30% probability displacement ellipsoids. 19
Figure 8. The π-π and C-H…π interactions in (4). Cg denotes the centroid of each ring [Symmetry codes: (i) 1-x, -y, -z; (ii) -x, -y, -z.] 20
Chart 1. Substituted Benzofurans 7
Chart 2. Substituted Naphthofurans 8
Scheme 1. Synthesis of compound (1) 10
Scheme 2. Synthesis of compound (2) 13
Scheme 3. Synthesis of compound (3) 16
Scheme 4. Synthesis of compound (4) 19