Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka,...
Transcript of Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka,...
![Page 1: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/1.jpg)
S1
Supporting Information
Synthesis of dihydroindeno[1,2-c]isochromene via cascade cyclization and
Friedel-Crafts reaction
Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah
Department of Chemistry, Indian Institute of Technology Guwahati, Assam-781039, India
Contents:
1. 1H and 13C NMR spectra of 3a-3p, 3r and 19F NMR of 3g, 3j S2-S20
2. X-crystallographic data of compound 3b S21-S22
3. HRMS Spectra of compounds 3a-3p, 3r S23-S31
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2016
![Page 2: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/2.jpg)
S2
1H NMR and 13C NMR spectra of compound 3a
O
![Page 3: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/3.jpg)
S3
1H NMR and 13C NMR spectra of compound 3b
O
Cl
![Page 4: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/4.jpg)
S4
1H NMR and 13C NMR spectra of compound 3c
O
Cl
![Page 5: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/5.jpg)
S5
1H NMR and 13C NMR spectra of compound 3d
O
Cl
![Page 6: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/6.jpg)
S6
1H NMR and 13C NMR spectra of compound 3e
O
Cl
Cl
![Page 7: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/7.jpg)
S7
1H NMR and 13C NMR spectra of compound 3f
O
Br
![Page 8: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/8.jpg)
S8
1H NMR and 13C NMR spectra of compound 3g
O
F
![Page 9: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/9.jpg)
S9
19F NMR spectrum of compound 3g
O
F
![Page 10: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/10.jpg)
S10
1H NMR and 13C NMR spectra of compound 3h
O
MeOOC
![Page 11: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/11.jpg)
S11
1H NMR and 13C NMR spectra of compound 3i
O
NC
![Page 12: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/12.jpg)
S12
1H NMR and 13C NMR spectra of compound 3j
O
F3C
![Page 13: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/13.jpg)
S13
19F NMR spectrum of compound 3j
O
F3C
![Page 14: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/14.jpg)
S14
1H NMR and 13C NMR spectra of compound 3k
O
NO2
![Page 15: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/15.jpg)
S15
1H NMR and 13C NMR spectra of compound 3l
O
Me
![Page 16: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/16.jpg)
S16
1H NMR and 13C NMR spectra of compound 3m
O
Me2N
![Page 17: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/17.jpg)
S17
1H NMR and 13C NMR spectra of compound 3n
![Page 18: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/18.jpg)
S18
1H NMR and 13C NMR spectra of compound 3o
![Page 19: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/19.jpg)
S19
1H NMR and 13C NMR spectra of compound 3p
![Page 20: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/20.jpg)
S20
1H NMR and 13C NMR spectra of compound 3r
![Page 21: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/21.jpg)
S21
The crystal parameters of compound 3b
CCDC 1483531
Formula
Formula weight
T/K
Crystal system
Space group
a/Å
b/Å
c/Å
α/º
β/º
γ/º
V/Å3
Z
Abs. Coeff./mm-1
Abs. Correction
GOF on F2
Final R indices [I > 2σ(I)]
R indices [all data]
C22H14ClO
329.78
296(2)
Monoclinic
P21/c
17.382(19)
6.286(7)
17.040(18)
90.00
117.003(18)
90.00
1659(3)
4
0.234
multi-scan
1.016
R1 = 0.0683
wR2 = 0.1508
R1 = 0.0915
wR2 = 0.1664
![Page 22: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/22.jpg)
S22
ORTEP diagram of compound 3b, thermal ellipsoids are drawn on 50% probability level
![Page 23: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/23.jpg)
S23
HRMS spectrum of compound 3a
HRMS spectrum of compound 3b
![Page 24: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/24.jpg)
S24
HRMS spectrum of compound 3c
HRMS spectrum of compound 3d
![Page 25: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/25.jpg)
S25
HRMS spectrum of compound 3e
HRMS spectrum of compound 3f
![Page 26: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/26.jpg)
S26
HRMS spectrum of compound 3g
HRMS spectrum of compound 3h
![Page 27: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/27.jpg)
S27
HRMS spectrum of compound 3i
HRMS spectrum of compound 3j
![Page 28: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/28.jpg)
S28
HRMS spectrum of compound 3k
HRMS spectrum of compound 3l
![Page 29: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/29.jpg)
S29
HRMS spectrum of compound 3m
HRMS spectrum of compound 3n
![Page 30: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/30.jpg)
S30
HRMS spectrum of compound 3o
HRMS spectrum of compound 3p
![Page 31: Supporting Information · Friedel-Crafts reaction Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah Department of Chemistry, Indian Institute of Technology Guwahati,](https://reader036.fdocuments.us/reader036/viewer/2022071218/60526d06f2fcd87773639def/html5/thumbnails/31.jpg)
S31
HRMS spectrum of compound 3r