hrms spectra for reference synthesis of oxabicyclo … spectra for reference synthesis of oxabicyclo...
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![Page 1: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/1.jpg)
HRMS spectra for Reference
Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-
Ene Reaction
Pipas Saha, Paramartha Gogoi and Anil K. Saikia*
S1
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 2: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/2.jpg)
HRMS spectrum of 3a
S2
O
H3C
CH3
CH3
HH
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 3: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/3.jpg)
HRMS spectrum of 3b
S3
O
H3C
CH3
CH3
HH
Cl
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 4: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/4.jpg)
HRMS spectrum of 3c
S4
O
H3C
CH3
CH3
HH
Br
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 5: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/5.jpg)
HRMS spectrum of 3d
S5
O
H3C
CH3
CH3
HH
F
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 6: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/6.jpg)
HRMS spectrum of 3e
S6
O
H3C
CH3
CH3
HH
O2N
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 7: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/7.jpg)
HRMS spectrum of 3f
S7
O
H3C
CH3
CH3
HH
NO2
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 8: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/8.jpg)
HRMS spectrum of 3g
S8
O
H3C
CH3
CH3
HH
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 9: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/9.jpg)
HRMS spectrum of 3h
S9
O
H3C
CH3
CH3
HH
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 10: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/10.jpg)
HRMS spectrum of 3i
S10
O
H3C
CH3
CH3
HHO2N
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 11: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/11.jpg)
HRMS spectrum of 3j
S11
O
H3C
CH3
CH3
HH
MeOOC
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 12: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/12.jpg)
HRMS spectrum of 3k
S12
O
H3C
CH3
CH3
HH
HO
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 13: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/13.jpg)
HRMS spectrum of 3l
S13
O
H3C
CH3
CH3
HH
H3C
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 14: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/14.jpg)
HRMS spectrum of 3m
S14
O
H3C
CH3
CH3
HH
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 15: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/15.jpg)
HRMS spectrum of 3n
S15
O
H3C
CH3
CH3
HH
H3C
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 16: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/16.jpg)
HRMS spectrum of 3o
S16
O
H3C
CH3
CH3
HH
H3C
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 17: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/17.jpg)
HRMS spectrum of 3p
S17
O
H3C
CH3
CH3
HH
H3C
CH3
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 18: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/18.jpg)
HRMS spectrum of 3q
S18
O
H3C
CH3
CH3
HH
H3C
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 19: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/19.jpg)
HRMS spectrum of 3r
S19
O
H3C
CH3
CH3
HH
(CH2)14
H3C
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 20: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/20.jpg)
HRMS spectrum of 4a & 5a
S20
O CH3
CH2
H3C
H2C
+
O CH3
CH2
H3C
H2C
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 21: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/21.jpg)
HRMS spectrum of 4e
S21
O CH3
CH2
H3C
H2C
O2N
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 22: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/22.jpg)
HRMS spectrum of 4n & 5n
S22
O CH3
CH2
H3C
H2C
+
H3CO CH3
CH2
H3C
H2C
H3C
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 23: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/23.jpg)
HRMS spectrum of 4o & 5o
S23
O CH3
CH2
H3C
H2C
+
H3C
O CH3
CH2
H3C
H2C
H3C
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 24: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/24.jpg)
HRMS spectrum of 4p & 5p
S24
O CH3
CH2
H3C
H2C
+
H3C
H3C
O CH3
CH2
H3C
H2C
H3C
H3C
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 25: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/25.jpg)
HRMS spectrum of 4q & 5q
S25
On-C6H13 CH3
CH2
H3C
H2C
+
On-C6H13 CH3
CH2
H3C
H2C
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 26: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/26.jpg)
HRMS spectrum of 4r & 5r
S26
O(H2C)14 CH3
CH2
H3C
H2C +
H3C
O(H2C)14 CH3
CH2
H3C
H2C
H3C
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 27: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/27.jpg)
HRMS spectrum of 15
S27
O
O
HH
H
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 28: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/28.jpg)
HRMS spectrum of 17b
S28
O
H3C
CH3
CH3
HH
H3C
H3C
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 29: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/29.jpg)
HRMS spectrum of 18c & 19c
S29
O CH3
CH2
H3C
H2C
Ph
+
O CH3
CH2
H3C
H2C
Ph
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 30: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/30.jpg)
HRMS spectrum of 18d &19d
S30
O CH3
CH2
H3C
H2C
BnO
H3C
+
O CH3
CH2
H3C
H2C
BnO
H3C
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 31: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/31.jpg)
HRMS spectrum of 18e & 19e
H3C
H2C
p-MeO-C6H5
S31
O CH3
CH2
+
O CH3
CH
H3C
H2C
p-MeO-C6H5
H2
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 32: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/32.jpg)
HRMS spectrum of 18f & 19f
O CH3
CH2
H3C
H2C +
Cl
O CH3
CH
H3C
H2C
Cl
S32
2
H2
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
![Page 33: HRMS spectra for Reference Synthesis of Oxabicyclo … spectra for Reference Synthesis of Oxabicyclo [3.3.1]nonenes and Substituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction](https://reader033.vdocuments.site/reader033/viewer/2022050801/5acd51637f8b9ab10a8d83d8/html5/thumbnails/33.jpg)
HRMS spectrum of 18g & 19g
S33
O CH3
CH2
H3C
H2C +
Br
O CH3
CH2
H3C
H2C
Br
Electronic Supplementary Material (ESI) for Organdic and Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011