The Journal of Organic Chemistry
Note
white crystals which were left to dry for 15 min, then collected in a
round-bottom flask, and dried under high vacuum to afford pure 1-
H SO (16.2 g, 60 mmol, 78%). The reagent was collected and stored
(12) (a) Berkov-Zrihen, Y.; Herzog, I. M.; Benhamou, R. I.; Feldman,
M.; Steinbuch, K. F.; Shaul, P.; Lerer, S.; Eldar, A.; Fridman, M. Chem.
- Eur. J. 2015, 21, 4340. (b) Suzuki, K.; Daikoku, S.; Son, S.-H.; Ito, Y.;
Kanie, O. Carbohydr. Res. 2015, 406, 1. (c) Razgulin, A. V.; Mecozzi, S.
Carbohydr. Res. 2015, 406, 10. (d) Zhang, G.; Richardson, S. L.; Mao,
Y.; Huang, R. Org. Biomol. Chem. 2015, 13, 4149.
(13) Yan, R.-B.; Yang, F.; Wu, Y.; Zhang, L.-H.; Ye, X.-S. Tetrahedron
Lett. 2005, 46, 8993.
(14) Kitamura, M.; Kato, S.; Yano, M.; Tashiro, N.; Shiratake, Y.;
Sando, M.; Okauchi, T. Org. Biomol. Chem. 2014, 12, 4397.
(15) Suarez, J. R.; Trastoy, B.; Perez-Ojeda, M. E.; Marin-Barrios, R.;
Chiara, J. L. Adv. Synth. Catal. 2010, 352, 2515.
2
4
under N in the fridge. While discoloration of 1-H SO has not been
2
2
4
observed following its handling with metal utensils, plastic utensils are
suggested as a precaution.
1
+
H NMR (DMSO-d , 400 MHz) δ 14.29 (s, br, NH ), 13.11 (s,
6
−
HSO ), 9.08 (s, CH), 8.08 (t, J = 1.7 Hz, CH), 7.52 (dd, J = 1.7, 0.8
Hz, CH); C NMR (101 MHz; DMSO-d ) δ 138.6, 128.0, 119.9 (as
previously noted, up to 10% decomposition occurs in DMSO as
evidenced by additional peaks in both H NMR [9.01 (s, br, CH), 7.61
d, J = 0.8 Hz, CH)]; and C NMR [134.8, 119.8]). m/z (MALDI)
94 (MNa , 100%), 335 ([MeCN + MNa] , 30%); FTIR (neat) ν
4
13
6
20
1
13
(
2
2
1
+
+
max
(16) Goddard-Borger, E. D.; Stick, R. V. Org. Lett. 2007, 9, 3797.
(17) It is noted that the Lewis-type structures shown for the SO N
3
−1
176 (N ), 1301 (asymm. SO), 1125 (symm. SO) cm ; Mp:
3
2
02−105 °C (Lit. 105−108 °C). Observed data match literature
group do not indicate the bond orders or actual valencies.
20
values.
(18) Ye, H.; Liu, R.; Li, D.; Liu, Y.; Yuan, H.; Guo, W.; Zhou, L.;
Cao, X.; Tian, H.; Shen, J.; Wang, P. G. Org. Lett. 2013, 15, 18.
(19) Dufour, E.; Moni, L.; Bonnat, L.; Chierici, S.; Garcia, J. Org.
Biomol. Chem. 2014, 12, 4964.
ASSOCIATED CONTENT
Supporting Information
■
*
S
(20) Bachl, J.; Mayr, J.; Sayago, F. J.; Cativiela, C.; Díaz, D. D. Chem.
Commun. 2015, 51, 5294.
(
(
21) Goddard-Borger, E. D.; Stick, R. V. Org. Lett. 2011, 13, 2514.
22) Fischer, N.; Goddard-Borger, E. D.; Greiner, R.; Klapotke, T.
1
13
Copies of 1-H SO H and C NMR, mass spectra, and
̈
2
4
M.; Skelton, B. M.; Stierstorfer, J. J. Org. Chem. 2012, 77, 1760.
23) Stevens, M. Y.; Sawant, R. T.; Odell, L. R. J. Org. Chem. 2014,
9, 4826.
24) Isidro-Llobet, A.; Georgiou, K. H.; Galloway, W. R. J. D.;
Giacomini, E.; Hansen, M. R.; Mendez-Abt, G.; Tan, Y.; Carro, L. Org.
Biomol. Chem. 2015, 13, 4570.
25) Perez, A. J.; Wesche, F.; Adihou, H.; Bode, H. B. Chem. - Eur. J.
016, 22, 639.
26) Byrne, J. P.; Martínez-Calvo, M.; Peacock, R. D.; Gunnlaugsson,
T. Chem. - Eur. J. 2016, 22, 486.
27) Griffiths, J. J. J. Chem. Soc. C 1971, 3191.
FTIR. Stepwise procedure with accompanying color
photographs following Method B to allow for ease of
protocol utilizing 1-H SO (PDF)
(
7
(
2
4
́
(
2
(
AUTHOR INFORMATION
■
*
(
Present Address
Synthesis & Medicinal Chemistry Cluster, Keele University,
Keele, Staffordshire, ST5 5BG, UK.
§
(28) Bradley, D.; Williams, G.; Lawton, M. J. Org. Chem. 2010, 75,
8
351.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
The MRC [G902173] are thanked for project grant funding,
the Paterson Institute is thanked for supplementary stipend
support (to G.T.P.), and IBCarb (BBSRC Grant BB/L013762/
1) is thanked for an Early-Career Researcher award supporting
G.T.P.
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