Supplemental Data 1, synthesis of 1, 2, 4 and 1-iodo-2-phenylpropan-2-ol

and accurate mass data.

2,3-Diacetyl-2,3-diphenylsuccinonitrile, Compound 1.

A mixture of APAAN (15 g, 94 mmol) and activated manganese dioxide (15 g) in

dichloromethane (200 ml) was stirred at room temperature overnight. The

mixture was filtered and concentrated to dryness to give an orange solid (9.27g)

this was a mixture of dimers and other oxidation products. The mother liquor

obtained from the recrystallization (ethyl acetate/cyclohexane) of 2.0 g of the

orange solid was evaporated to dryness and the residue was washed with t-butyl

methyl ether to afford 1 as a beige solid (206 mg, 0.65 mmol); mp166-168 -oC.

(This synthesis was repeated a number of times). Prior to NMR analysis 1 was

cleaned up by preparative TLC (silica gel; cyclohexane/ethyl acetate, 200/10)

which yielded 90% 1 in dl form. 1H NMR (CDCl3), δ 7.47 (t; J = 7.8 Hz; 2H; Ar H),

7.37 (t; J = 7.8 Hz; 4H; Ar H), 7.05 (d; J = 7.8 Hz; 4H; Ar H), and 2.49 (s; 6H;

13
CH3); C NMR (CDCl3) δ 197.22 (C=O), 130.07 (Ar CH), 128.79 (Ar CH),

128.73 (ArCH), 127.85 (Ar C), 116.46 (CN) and 27.53 (CH3) ppm; HRMS, found

317.1281, mass accuracy Delta (ppm) -0.99, (theor. for [M+H]+, C20H17N2O2+,

317.1285).
2-Methyl-1-phenyl-1,3 dicarbonitrile-1H-indene, Compound 2.

2,3-Diacetyl-2,3-diphenylsuccinonitrile (200 mg, 0.63 mmol) was pyrolysed in a

100 ml round bottomed flask using a heat gun (Dewalt) on maximum setting

(600oC) for approximately 30 seconds so as to maximize pyrolysis products.

During this preparative pyrolysis, some effervescence was noted and a brown tar

was obtained. This was purified by preparative TLC (silica gel; cyclohexane/ethyl

acetate, 200/10) to afford 2 as almost colourless oil which solidified on standing

(23 mg, 0.09 mmol ): mp 79-81oC; 1H NMR (CDCl3) δ 7.57 (d; J = 7.6 Hz; 1H;

Ar H), 7.50-7.53 (m; 1H; Ar H), 7.35-7.42 (m; 5H; Ar H), 7.21-7.23 (m; 2H, Ar H)
13
and 2.24 (s; 3H; CH3); C NMR (CDCl3) δ 159.91 (C indene), 143.43 (Ar CH),

138.43 (Ar CH), 132.78 (Ar C), 129.93 (Ar CH), 129.66 (Ar C), 129.26 (Ar C),

128.61 (Ar C), 125.88 (Ar C), 124.46 (Ar C), 120.72 (Ar C), 116.78 (CN),

113.00 (CN), 115.10 (C indene), 58.39 (C indene), and 13.44 (CH3) ppm; HRMS,

found 255.0922, mass accuracy Delta (ppm) 2.22 (theor. for [M-H]-, C18H11N2,

255.0917).

1-Iodo-2-phenylpropan-2-ol

Mixture (B) (500 mg) from the AMS, Oxone and NaI route was purified by

preparative TLC (silica gel; cyclohexane) to afford a yellow oil (198 mg, 0.75

mmol): 1H NMR (CDCl3) δ 7.47 (d; J = 7.4 Hz; 2 H; Ar H), 7.39 (tr; J = 7.4 Hz; 2

H; Ar H), 7.32 (tr; J = 7.4 Hz; 1 H; Ar H), 3.66 (AB q; J=10.2 Hz; 2 H; CH2) and
13
1.66 (s, 3 H; CH3) ppm; C NMR (CDCl3) δ 13C NMR 144.09 (Ar C), 128.28 (Ar

CH), 127.33 (Ar CH), 124.56 (Ar CH), 72.49 (C(CH3)OH), 28.82 (CH3) and

24.09 (CH2) ppm.

1-Phenyl-N-(1-phenylethyl)propan-2-amine, Compound 4.

A mixture of amphetamine freebase (2.16 g, 16 mmol) and acetophenone (1.92

g, 16 mmol) in toluene (75 mL) was refluxed, with azeotropic removal of water,

for 6 hr. The toluene was then removed by distillation to afford a yellow oil (2.63

g). A portion of this crude 1-phenyl-N-(1-phenylethylidene)propan-2-amine (2.00

g), sodium borohydride (1.50 g) and ethanol (60 mL) was stirred overnight at

room temperature. The ethanol was removed under vacuum. The residue was

partitioned between dichloromethane and water. The organic layer was collected,

dried (anhydrous magnesium sulfate) and the solvent was removed to afford an

almost colorless oil (1.95 g). A portion (600 mg) was purified by preparative TLC

(silica gel; ethyl acetate) and converted to the hydrochloride salt (2M hydrogen

chloride in diethyl ether) and triturated with t-butyl ether ether to afford a colorless

powder (50 mg, 0.21 mmol): mp 210-212 oC; 1H NMR (d6 DMSO) δ 7.70-7.74 (m;

2 H; Ar H), 7.41-7.51 (m; 3 H; Ar H), 7.20-7.29 (m; 3 H; Ar H), 7.22 (d; J = 6.8

Hz; 2 H; Ar H), 4.59-4.64 (m; 1 H; CH), 3.38-3.42 (m; 1 H; one H from CH2),

2.90-2.98 (m; 1 H; CH), 2.56-2.62 (m; 1 H; one H from CH2), 1.65 (d; J = 5.3 Hz;
13
2 H; CH3) and 1.12 (d; J = 5.4 Hz; 2 H; CH3) ppm; C NMR (d6 DMSO) δ 137.44

(Ar C), 136.86 (Ar C), 129,02 (Ar CH), 128.94 (Ar CH), 128.86 (Ar CH),

128.53 (Ar CH), 127.78 (Ar CH), 126.69 (Ar CH), 54.32 (CH), 52.58 (CH), 37.40

(CH2), 19.88 (CH3) and 16.06 (CH3) ppm; HRMS, found 240.1756 (theor. for

[M+H]+, mass accuracy Delta (ppm) 4.01, C17H22N+, 240.1747).