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1 Supporting Information An Experimental and Computational Approach to Understanding the Reactions of Acyl Nitroso Compounds in [4+2]-Cycloadditions Duangduan Chaiyaveij, Andrei S. Batsanov, Mark A. Fox, Todd B. Marder and Andrew Whiting * * andy.whiting@durham.ac.uk Contents 1. 1 H-NMR, 13 C-NMR spectroscopic data (Figures S1-S45)...S2-S46 2. X-ray crystallographic data (Figures S46-S48, Table S1)...S47-S49 3. Calculations (Tables S2-S9)...S50-S61 S1
2 Figure S1. Phenyl hydroxycarbamate 1 (crude) S2
3 Figure S2.1-Hydroxy-3-phenylurea 2 S3
4 Figure S3. (R)-1-Hydroxy-3-(1-phenylethyl)urea 3 S4
5 Figure S4. N-Hydroxy-2-phenylacetamide 4 S5
6 Figure S5. N-Hydroxy-3-phenylpropanamide 5 S6
7 Figure S6. N-Hydroxy-4-phenylbutanamide 6 S7
8 Figure S7. N-Hydroxy-5-phenylpentanamide 7 S8
9 Figure S8. N-Hydroxybenzamide 8 S9
10 Figure S9. 2-Pyridinehydroxamic acid 9 S10
11 Figure S10. 3-Pyridinehydroxamic acid 10 S11
12 Figure S11. N-Hydroxy-2-(pyridin-2-yl)acetamide 11 (crude) S12
13 Figure S12. 2-Amino-N-hydroxybenzamide 12 S13
14 Figure S13. N-Hydroxy-N -[(R)-1-Phenylethyl]-N-[(R)-1-Phenylethylcarbamoyl]urea 13 S14
15 Figure S14. Phenyl-2-oxa-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate 14 (Table 1, Entry 1, GP2) S15
16 Figure S15. N-Phenyl-2-oxa-3-azabicyclo[2.2.2]oct-5-ene-3-carboxamide 15 (Table 1, Entry 2, GP2) S16
17 Figure S16. N-[(R)-1-Phenylethyl]-2-oxa-3-azabicyclo[2.2.2]oct-5-ene-3-carboxamide 16 (Table 1, Entry 3, GP2) S17
18 Figure S17. 2-Oxa-3-azabicyclo[2.2.2]oct-5-en-3-yl-2-phenyl-ethanone 17 (Table 1, Entry 4, GP1) S18
19 Figure S18. 2-Oxa-3-azabicyclo[2.2.2]oct-5-en-3-yl)-3-phenylpropan-1-one 18 (Table 1, Entry 5, GP3) S19
20 Figure S19. 2-Oxa-3-azabicyclo[2.2.2]oct-5-en-3-yl)-4-phenylbutan-1-one 19 (Table 1, Entry 6, GP1) S20
21 Figure S20. 2-Oxa-3-azabicyclo[2.2.2]oct-5-en-3-yl)-5-phenylpentan-1-one 20 (Table 1, Entry 7, GP1) S21
22 Figure S21. 2-Oxa-3-azabicyclo[2.2.2]oct-5-en-3-yl(phenyl)methanone 21 (Table 1, Entry 8, GP1) S22
23 Figure S22. 2-Oxa-3-azabicyclo[2.2.2]oct-5-en-3-yl(pyridin-2-yl) methanone 22 (Table 1, Entry 9, GP1) S23
24 Figure S23. 2-Oxa-3-azabicyclo[2.2.2]oct-5-en-3-yl(pyridin-3-yl)methanone 23 (Table 1, Entry 10, GP1) S24
25 Figure S24. Phenyl-4,5-dimethyl-3,6-dihydro-2H-1,2-oxazine-2-carboxylate 24 (Table 1, Entry 11, GP2) S25
26 Figure S25. 4,5-Dimethyl-N-phenyl-3,6-dihydro-2H-1,2-oxazine-2-carboxamide 25 (Table 1, Entry 12, GP2) H H S26
27 Figure S26. (R)-4,5-Dimethyl-N-(1-phenylethyl)-3,6-dihydro-2H-1,2-oxazine-2-carboxamide 26 (Table 1, Entry 13, GP2) S27
28 Figure S27. 1-(4,5-Dimethyl-3,6-dihydro-2H-1,2-oxazin-2-yl)-2-phenylethanone 27 (Table 1, Entry 14, GP1) S28
29 Figure S28. 1-(4,5-Dimethyl-3,6-dihydro-2H-1,2-oxazin-2-yl)-3-phenylpropan-1-one 28 (Table 1, Entry 15, GP1) S29
30 Figure S29. 1-(4,5-Dimethyl-3,6-dihydro-2H-1,2-oxazin-2-yl)-4-phenylbutan-1-one 29 (Table 1, Entry 16, GP1) S30
31 Figure S30. 1-(4,5-Dimethyl-3,6-dihydro-2H-1,2-oxazin-2-yl)-5-phenylpentan-1-one 30 (Table 1, Entry 17, GP1) S31
32 Figure S31. (4,5-Dimethyl-3,6-dihydro-2H-1,2-oxazin-2-yl)(phenyl)methanone 31 (Table 1, Entry 18, GP1) S32
33 Figure S32. (4,5-Dimethyl-3,6-dihydro-2H-1,2-oxazin-2-yl)(pyridin-2-yl)methanone 32 (Table 1, Entry 19, GP1) S33
34 Figure S33. (4,5-Dimethyl-3,6-dihydro-2H-1,2-oxazin-2-yl)(pyridin-3-yl)methanone 33 (Table 1, Entry 20, GP1) S34
35 Figure S34. Phenyl 2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate 36 (Table 2, Entry 1) S35
36 Figure S35. (9S,10S)-Phenyl-9,10-dimethyl-9,10-dihydro-9,10-(epoxy-imino)-anthracene-11-carboxylate 37 (Table 2, Entry 2) S36
37 Figure S36. Phenyl 3,6-dimethyl-3,6-dihydro-2H-1,2-oxazine-2-carboxylate 38 (Table 2, Entry 3) S37
38 Figure S37. Phenyl 3,6-diphenyl-3,6-dihydro-2H-1,2-oxazine-2-carboxylate 39 (Table 2, Entry 4) S38
39 Figure S38. Phenyl-6-(hydroxymethyl)-3-methyl-3,6-dihydro-2H-1,2-oxazine-2-carboxylate 40 (Table 2, Entry 5) S39
40 Figure S39. Mixture of phenyl-6-(hydroxymethyl)-3-methyl-3,6-dihydro-2h-1,2-oxazine-2-carboxylate 40 and phenyl 3-(hydroxymethyl)-6-methyl-3,6-dihydro-2H-1,2-oxazine-2-carboxylate 41. (Table 2, Entry 5) S40
41 Figure S40. Mixture of phenyl 4-methyl-3,6-dihydro-2H-1,2-oxazine-2-carboxylate 42 and phenyl 5- methyl-3,6-dihydro-2h-1,2-oxazine-2-carboxylate 43 (Table 2, Entry 6) S41
42 Figure S41. N-Phenyl-2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxamide 45 (Table 2, Entry 7) S42
43 Figure S42. 3,6-Dimethyl-N-phenyl-3,6-dihydro-2H-1,2-oxazine-2-carboxamide 47 (Table 2, Entry 9) H 9 H S43
44 Figure S43. N-3,6-Triphenyl-3,6-dihydro-2H-1,2-oxazine-2-carboxamide 48 (susceptible to cycloreversion at room temperature) (Table 2, Entry 10) S44
45 Figure S44. 6-(Hydroxymethyl)-3-methyl-N-phenyl-3,6-dihydro-2H-1,2-oxazine-2-carboxamide 49 (Table 2, Entry 11) S45
46 Figure S45. Mixture of 4-Methyl-N-phenyl-3,6-dihydro-2H-1,2-oxazine-2-carboxamide 51 and 5- methyl-n-phenyl-3,6-dihydro-2h-1,2-oxazine-2-carboxamide 52 (Table 2, Entry 12) H H H H S46
47 X-ray Crystallography Figure S46. The asymmetric units in the crystal structures of 2, 3, 9 H2O, 15, 16, 21, 25, 32 and 36. Thermal ellipsoids are drawn at the 50% probability level. S47
48 Figure S47. The disorder of molecule 17 in crystal (top, H atoms omitted) and two alternative components, having occupancies 0.55 (A) and 0.45 (B) Figure S48. The disorder of molecule 14 in crystal (top, H atoms omitted) and one of the two alternative components related by the crystallographic mirror plane. Mirror-generated atoms are primed S48
49 Table S1. Crystal data and experimental details Compound H 2 O CCDC Formula C 7 H 8 N 2 O 2 C 15 H 18 N 2 O 2 C 6 H 6 N 2 O 2 H 2 O C 13 H 13 NO 3 C 13 H 14 N 2 O 2 C 9 H 12 N 2 O 2 C 14 H 15 NO 2 C 13 H 13 NO 2 C 13 H 16 N 2 O 2 C 12 H 14 N 2 O 2 C 12 H 11 NO 3 M T/K Crystal system triclinic tetragonal monoclinic orthorhombic orthorhombic orthorhombic monoclinic monoclinic orthorhombic triclinic monoclinic Space group P-1 (#2) P (#92) C2/c (#15) Pnma (#62) Pna2 1 (#33) P (#19) P2 1 /c (#14) P2 1 /c (#14) Pbca (#61) P-1 (#2) P2 1 /c (#14) a/å (4) (9) (16) (6) (6) (3) (10) (9) (8) (6) (5) b/å (5) (9) (3) (8) (5) (5) (5) (13) (5) (6) (7) c/å (18) (3) (16) (12) (8) (13) (12) (14) (13) (7) (19) α/ (18) (3) 90 β/ (18) (4) (13) (10) (3) (15) γ/ (16) (3) 90 V/Å (10) (7) (2) (15) (12) (16) (16) (2) (3) (7) (16) Z D calc./g cm θ max/ Refls. total Refls. unique Refls. I>2σ(I) R(int) Parameters wr 2 (all data) R 1 [I>2σ(I)] S49
50 Computations Table S2. Comparison of bond lengths (Å) between X-ray and computed geometries for 14, 15 and R = Ph 15 R = NHPh 21 R = OPh Bond Observed Calculated Observed Calculated Observed Calculated Cyclic N3-O Cyclic O2-C Cyclic N3-C Cyclic C=C Non-cyclic N3-C Non-cyclic C9=O Non-cyclic C9-R S50
51 Table S3. Various total energies in hartrees for true and transition state minima in the reaction pathways of HCONO and butadiene (Figure 3). trans-nitroso trans diene diene (TS) cis diene Electronic Energies Electronic + Zero Point Energies Electronic + Thermal Energies Electronic + Thermal Enthalpies Electronic + Thermal Gibbs Free Energies I TS-I/II II TS-II/III III Electronic Energies Electronic + Zero Point Energies Electronic + Thermal Energies Electronic + Thermal Enthalpies Electronic + Thermal Gibbs Free Energies I(LM) TS-I/II(LM) II(LM) TS-II/III III Electronic Energies Electronic + Zero Point Energies Electronic + Thermal Energies Electronic + Thermal Enthalpies Electronic + Thermal Gibbs Free Energies S51
52 Table S4. Relative energies in kcal mol -1 from various total energies for true and transition state minima in the reaction pathways of HCONO and butadiene (Figure 3). I TS-I/II II TS-II/III III Electronic Energies Electronic + Zero Point Energies Electronic + Thermal Energies Electronic + Thermal Enthalpies Electronic + Thermal Gibbs Free Energies I(LM) TS-I/II(LM) II(LM) TS-II/III III Electronic Energies Electronic + Zero Point Energies Electronic + Thermal Energies Electronic + Thermal Enthalpies Electronic + Thermal Gibbs Free Energies Table S5. Relative energies in kcal mol -1 for s-trans, s-cis and transition state geometries of nitroso reactants. trans TS cis HCONO MeOCONO MeNHCONO S52
53 Table S6. Relative energies in kcal mol -1 for nitroso-diels-alder pathways of cyclohexadiene and anthracene (Figure 5). Pathway Type cis-diene + Nitroso Local Minimum Transition state Product II II(LM) TSII/III III Cyclohexadiene s-trans-meocono Endo DA s-cis-meocono Endo DA s-trans-meocono Exo DA s-cis-meocono Exo DA s-trans-menhcono Endo DA s-cis-menhcono Endo DA s-trans-menhcono Exo DA s-cis-menhcono Exo DA ,10-Dimethylanthracene s-trans-meocono s-cis-meocono s-trans-menhcono s-cis-menhcono S53
54 Table S7. Relative energies in kcal mol -1 for nitroso-diels-alder pathways of non-cyclic dienes (Figures 5 and 6). Pathway Type trans-diene + Transition cis-diene + Transition Product Nitroso state Nitroso state I(LM) TSI/II(LM) II(LM) TSII/III III CH 2 =CMeCMe=CH 2 s-trans-meocono Endo DA s-cis-meocono Endo DA s-trans-menhcono Endo DA s-cis-menhcono Endo DA s-trans-meocono Exo DA s-cis-meocono Exo DA s-trans-menhcono Exo DA s-cis-menhcono Exo DA MeCH=CHCH=CHMe s-trans-meocono Endo DA s-cis-meocono Endo DA s-trans-menhcono Endo DA s-cis-menhcono Endo DA PhCH=CHCH=CHPh s-trans-meocono Endo DA s-cis-meocono Endo DA s-trans-menhcono Endo DA CH 2 =CMeCH=CH 2 s-trans-meocono Endo DA distal s-cis-meocono Endo DA distal s-trans-meocono Endo DA proximal s-cis-meocono Endo DA proximal s-trans-menhcono Endo DA distal s-cis-menhcono Endo DA distal s-trans-menhcono Endo DA proximal s-cis-menhcono Endo DA proximal S54
55 Table S8. Relative energies in kcal mol -1 for nitroso-ene pathways of 2,3-dimethylbutadiene and 2-methylbutadiene (Figure 7). Local Minimum Transition state Intermediate Transition state Product I(LM) or II(LM) TSI/IV or TSII/IV IV TSIV/V V trans-ch 2 =CMeCMe=CH 2 s-trans-meocono cis-ch 2 =CMeCMe=CH 2 s-trans-meocono trans-ch 2 =CMeCMe=CH 2 s-trans-menhcono cis-ch 2 =CMeCMe=CH 2 s-trans-menhcono trans-ch 2 =CMeCH=CH 2 s-trans-meocono cis-ch 2 =CMeCH=CH 2 s-trans-meocono trans-ch 2 =CMeCH=CH 2 s-trans-menhcono cis-ch 2 =CMeCH=CH 2 s-trans-menhcono S55
56 Table S9. Transition state energies in hartrees for nitroso-diels-alder and nitroso-ene pathways of 2,3-dimethylbutadiene and 2- methylbutadiene. Diels-Alder product Transition state Transition state Transition state Transition state III I/II + nitroso TSII/III endo TSII/III exo TSI/IV cis-ch 2 =CMeCMe=CH 2 s-trans-meocono cis-ch 2 =CMeCMe=CH 2 s-cis-meocono trans-ch 2 =CMeCMe=CH 2 s-trans-meocono cis-ch 2 =CMeCMe=CH 2 s-trans-menhcono cis-ch 2 =CMeCMe=CH 2 s-cis-menhcono trans-ch 2 =CMeCMe=CH 2 s-trans-menhcono cis-ch 2 =CMeCH=CH 2 s-trans-meocono Proximal cis-ch 2 =CMeCH=CH 2 s-cis-meocono Proximal cis-ch 2 =CMeCH=CH 2 s-trans-meocono Distal cis-ch 2 =CMeCH=CH 2 s-cis-meocono Distal trans-ch 2 =CMeCH=CH 2 s-trans-meocono cis-ch 2 =CMeCH=CH 2 s-trans-menhcono Proximal cis-ch 2 =CMeCH=CH 2 s-cis-menhcono Proximal cis-ch 2 =CMeCH=CH 2 s-trans-menhcono Distal cis-ch 2 =CMeCH=CH 2 s-cis-menhcono Distal trans-ch 2 =CMeCH=CH 2 s-trans-menhcono S56
57 Cartesian Coordinates of Optimized Geometries 22 anti-form A C C C C H H H H C C H H N O H H C O C C C C H H H C H N syn-form B C C C C H H H H C C H H N O H H C O C C C C S57
58 H H H C H N Transition state geometry between anti-form A and syn-form B C C C C H H H H C C H H N O H H C O C C C C H H H C H N I(LM) HCONO:trans-H 2 C=CHCH=CH 2 adduct C C C H C O N C O H H H H H H S58
59 TS-I/II(LM) HCONO:H 2 C=CHCH=CH 2 adduct C C C H C O N C O H H H H H H II(LM) HCONO:cis-H 2 C=CHCH=CH 2 adduct C C C H C O N C O H H H H H H TS-II/III(LM) HCONO:H 2 C=CHCH=CH 2 endo-nda transition state C C C H C O N C O H H H H H H S59
60 III HCONO:H 2 C=CHCH=CH 2 oxazine NDA product C C C H C O N C O H H H H H H S60
61 References S61
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