Oxidation of alcohols with 1-decyl-4-aza-1-azonia-bicyclo[2.2.2]-octane chlorochromate under conventional and solvent-free conditions

Article abstract of DOI:10.1134/S1070428006060054

1-Decyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate was proposed as a mild and efficient reagent for oxidation of alcohols to the corresponding carbonyl compounds in boiling acetonitrile or under solvent-free conditions at room temperature. The experimental procedure is simple, and the products are isolated in good to excellent yields. Pleiades Publishing, Inc., 2006.

Full text of DOI:10.1134/S1070428006060054

2
[LGDWLRQꢀRIꢀ$OFRKROVꢀZLWKꢀꢁꢂ'HF\OꢂꢃꢂD]DꢂꢁꢂD]RQLDꢂꢀ
ELF\FOR>ꢄꢅꢄꢅꢄ@ꢂRFWDQHꢀ&KORURFKURPDWHꢀXQGHUꢀ&RQYHQWLRQDOꢀꢀ
DQGꢀ6ROYHQWꢂ)UHHꢀ&RQGLWLRQVꢆꢀ
$ꢅꢀ5ꢅꢀ+DMLSRXU ꢇꢀꢀ+ꢅꢀ5ꢅꢀ%DJKHUL ꢇꢀꢀDQGꢀꢀ$ꢅꢀ(ꢅꢀ5XRKR
ꢂ3KDUPDFHXWLFDOꢀ5HVHDUFKꢀ/DERUDWRU\ꢁꢀ&ROOHJHꢀRIꢀ&KHPLVWU\ꢁꢀ,VIDKDQꢀ8QLYHUVLW\ꢀRIꢀ7HFKQRORJ\ꢁꢀ,VIDKDQꢁꢀꢂꢃꢄꢅꢆꢀ,UDQꢀ
ꢂ'HSDUWPHQWꢀRIꢀ3KDUPDFRORJ\ꢁꢀ0HGLFDOꢀ6FKRROꢁꢀ8QLYHUVLW\ꢀRIꢀ:LVFRQVLQꢁꢀꢀ
ꢄꢇꢈꢈꢀ8QLYHUVLW\ꢀ$YHQXHꢁꢀ0DGLVRQꢁꢀ:,ꢁꢀꢅꢇꢉꢈꢆꢊꢄꢅꢇꢋꢀ86$ꢀ
HꢊPDLOꢌꢀKDML#FFꢍLXWꢍDFꢍLUꢀ
5
HFHLYHGꢂ1RYHPEHUꢂꢃꢄꢅꢂꢆꢄꢄꢁꢂ
$
EVWUDFW²ꢇꢈ'HF\OꢈꢁꢈD]DꢈꢇꢈD]RQLDELF\FOR>ꢆꢉꢆꢉꢆ@RFWDQHꢂFKORURFKURPDWHꢂZDVꢂSURSRVHGꢂDVꢂDꢂPLOGꢂDQGꢂHIILFLHQWꢂ
UHDJHQWꢂIRUꢂR[LGDWLRQꢂRIꢂDOFRKROVꢂWRꢂWKHꢂFRUUHVSRQGLQJꢂFDUERQ\OꢂFRPSRXQGVꢂLQꢂERLOLQJꢂDFHWRQLWULOHꢂRUꢂXQGHUꢂ
VROYHQWꢈIUHHꢂFRQGLWLRQVꢂDWꢂURRPꢂWHPSHUDWXUHꢉꢂ7KHꢂH[SHULPHQWDOꢂSURFHGXUHꢂLVꢂVLPSOHꢅꢂDQGꢂWKHꢂSURGXFWVꢂDUHꢂ
LVRODWHGꢂLQꢂJRRGꢂWRꢂH[FHOOHQWꢂ\LHOGVꢉꢂ
'2,ꢈꢂꢇꢄꢉꢇꢇꢃꢁꢓ6ꢇꢄꢐꢄꢁꢆꢀꢄꢄꢏꢄꢏꢄꢄꢎꢁꢂ
2
[LGDWLRQꢂRIꢂRUJDQLFꢂFRPSRXQGVꢂLVꢂRQHꢂRIꢂWKHꢂPRVWꢂ SRXQGVꢂ>ꢇꢆ±ꢃꢁ@ꢅꢂLQꢂWKHꢂSUHVHQWꢂDUWLFOHꢂZHꢂGHVFULEHꢂꢂ
LPSRUWDQWꢂUHDFWLRQVꢂLQꢂPRGHUQꢂRUJDQLFꢂV\QWKHVLVꢉꢂ DQꢂHIIHFWLYHꢅꢂUDSLGꢅꢂPLOGꢅꢂDQGꢂVHOHFWLYHꢂSURFHGXUHꢂIRUꢂ
DULRXVꢂR[LGDQWVꢂKDYHꢂEHHQꢂUHSRUWHGꢂLQꢂWKHꢂOLWHUDWXUHꢂ WKHꢂR[LGDWLRQꢂRIꢂDOFRKROVꢂWRꢂWKHꢂFRUUHVSRQGLQJꢂFDUERQ\Oꢂ
ꢇ±ꢇꢇ@ꢉꢂ+RZHYHUꢅꢂPRVWꢂRIꢂWKHPꢂVXIIHUꢂIURPꢂDWꢂOHDVWꢂRQHꢂ FRPSRXQGVꢂXVLQJꢂꢇꢈGHF\OꢈꢁꢈD]DꢈꢇꢈD]RQLDELF\FORꢈ
RIꢂWKHꢂIROORZLQJꢂGLVDGYDQWDJHVꢋꢂꢌꢇꢍꢂKLJKꢂFRVWꢂRIꢂSUHꢈ
>ꢆꢉꢆꢉꢆ@RFWDQHꢂFKORURFKURPDWHꢂꢌ,,,ꢍꢉꢂ7KLVꢂR[LGDQWꢂLVꢂ
9
>
SDUDWLRQVꢅꢂꢌꢆꢍꢂORQJꢂUHDFWLRQꢂWLPHꢅꢂꢌꢃꢍꢂK\JURVFRSLFLW\ꢅꢂ UHDGLO\ꢂSUHSDUHGꢂLQꢂKLJKꢂ\LHOGꢂE\ꢂGURSZLVHꢂDGGLWLRQꢂRIꢂ
ꢌꢁꢍꢂKLJKꢂDFLGLW\ꢅꢂꢌꢎꢍꢂLQVWDELOLW\ꢅꢂꢌꢏꢍꢂORZꢂVHOHFWLYLW\ꢅꢂꢌꢐꢍꢂ DꢂVROXWLRQꢂRIꢂFKURPLXPꢌ9,ꢍꢂR[LGHꢂLQꢂꢏꢂ1ꢂK\GURFKORULFꢂ
SKRWRVHQVLWLYLW\ꢅꢂꢌꢀꢍꢂGDQJHURXVꢂSURFHGXUHVꢂIRUꢂWKHLUꢂ DFLGꢂWRꢂDQꢂDTXHRXVꢂVROXWLRQꢂRIꢂꢇꢈGHF\OꢈꢁꢈD]DꢈꢇꢈD]RQLDꢈ
SUHSDUDWLRQꢅꢂDQGꢂꢌꢑꢍꢂODERULRXVꢂZRUNꢈXSꢂSURFHGXUHVꢉꢂ ELF\FOR>ꢆꢉꢆꢉꢆ@RFWDQHꢂFKORULGHꢂꢌ,,ꢍꢂDWꢂURRPꢂWHPSHUDWXUHꢂ
&
KURPLXPꢌ9,ꢍꢂFRPSRXQGVꢂDUHꢂWKHꢂPRVWꢂZLGHO\ꢂXVHGꢂ ꢌ6FKHPHꢂꢇꢍꢉꢂ7KHꢂSURGXFWꢂLVꢂILOWHUHGꢂRIIꢂDQGꢂGULHGꢉꢂ,WꢂLVꢂ
WUDQVLWLRQꢂPHWDOꢂR[LGDQWVꢂLQꢂDTXHRXVꢂVROXWLRQꢒꢂWKHLUꢂ DQꢂRUDQJHꢂSRZGHUꢂZKLFKꢂFDQꢂEHꢂVWRUHGꢂIRUꢂVHYHUDOꢂ
VWUXFWXUHꢂGHSHQGVꢂRQꢂWKHꢂFRQFHQWUDWLRQꢂDQGꢂS+ꢉꢂ,Qꢂ PRQWKVꢂZLWKRXWꢂORVVꢂLQꢂDFWLYLW\ꢉꢂ&RPSRXQGꢂ,,,ꢂLVꢂ
VROXEOHꢂLQꢂDFHWRQLWULOHꢅꢂDFHWRQHꢅꢂDQGꢂGLPHWK\OIRUPꢈ
DPLGHꢅꢂVOLJKWO\ꢂVROXEOHꢂLQꢂFKORURIRUPꢅꢂHWK\OꢂDFHWDWHꢅꢂ
DQGꢂPHWK\OHQHꢂFKORULGHꢅꢂDQGꢂLQVROXEOHꢂLQꢂFDUERQꢂWHWUDꢈ
FKORULGHꢅꢂQꢈKH[DQHꢅꢂDQGꢂGLHWK\OꢂHWKHUꢉꢂ
GLOXWHꢂVROXWLRQꢅꢂPRQRPHULFꢂDFLGꢂFKURPDWHꢂLRQꢂLVꢂ
SUHVHQWꢅꢂZKLOHꢂGLFKURPDWHꢂLRQꢂSUHGRPLQDWHVꢂDVꢂWKHꢂFRQꢈ
FHQWUDWLRQꢂLQFUHDVHVꢉꢂ,WꢂLVꢂEHOLHYHGꢂWKDWꢂR[LGDWLRQꢂRIꢂ
DOFRKROVꢂLQYROYHVꢂLQWHUPHGLDWHꢂIRUPDWLRQꢂRIꢂUDGLFDOꢂ
VSHFLHVꢂUHVXOWLQJꢂIURPꢂWKHꢂVXEVWUDWHꢂUHDFWLRQꢂZLWKꢂꢂ
9DULRXVꢂSULPDU\ꢂDQGꢂVHFRQGDU\ꢂDOFRKROVꢂZHUHꢂ
&
&
Uꢌ9,ꢍꢉꢂ7KLVꢂVFKHPHꢂDOVRꢂLPSOLHVꢂSDUWLFLSDWLRQꢂRIꢂꢂ R[LGL]HGꢂZLWKꢂUHDJHQWꢂ,,,ꢂLQꢂERLOLQJꢂDFHWRQLWULOHꢂLQꢂWKHꢂ
Uꢌ9ꢍꢂGHULYDWLYHVꢂ>ꢇꢇ@ꢉꢂ
6
FKHPHꢀꢁꢅꢀ
,
QꢂWKHꢂUHFHQWꢂ\HDUVꢅꢂUHDFWLRQVꢂXQGHUꢂVROYHQWꢈIUHHꢂ
FRQGLWLRQVꢂKDYHꢂUHFHLYHGꢂLQFUHDVLQJꢂDWWHQWLRQꢉꢂ7KHꢂ
PDLQꢂDGYDQWDJHVꢂRIꢂWKHVHꢂPHWKRGVꢅꢂDVꢂFRPSDUHGꢂWRꢂ
FRQYHQWLRQDOꢂKRPRJHQHRXVꢂUHDFWLRQVꢅꢂDUHꢂJUHDWHUꢂVHOHFꢈ
WLYLW\ꢅꢂKLJKHUꢂUDWHꢅꢂVLPSOHUꢂH[SHULPHQWDOꢂSURFHGXUHꢅꢂDQGꢂ
LVRODWLRQꢂRIꢂSXUHUꢂSURGXFWVꢂ>ꢇꢆ±ꢆꢏ@ꢉꢂ
,QꢂFRQWLQXDWLRQꢂRIꢂRXUꢂVWXGLHVꢂRQꢂWKHꢂGHYHORSPHQWꢂ
RIꢂHIILFLHQWꢂUHDJHQWVꢂIRUꢂR[LGDWLRQꢂRIꢂRUJDQLFꢂFRPꢈ
ꢊꢂꢂ7KHꢂWH[WꢂZDVꢂVXEPLWWHGꢂE\ꢂWKHꢂDXWKRUVꢂLQꢂ(QJOLVKꢉꢂ
ꢀꢁꢁꢂ

2
;,'$7,21ꢂꢂ2)ꢂꢂ$/&2+2/6ꢂꢂ:,7+ꢂꢂꢇꢈ'(&</ꢈꢁꢈ$=$ꢈꢇꢈ$=21,$%,&<&/2>ꢆꢉꢆꢉꢆ@2&7$1(ꢂ
ꢀꢁꢎꢂ
6
FKHPHꢀꢄꢅꢀ
SHWLQJꢂUHDFWLRQꢂWHFKQLTXHꢂJDYHꢂDOPRVWꢂWKHꢂVDPHꢂUHVXOWVꢂ
DVꢂWKRVHꢂREWDLQHGꢂLQꢂERLOLQJꢂDFHWRQLWULOHꢂZLWKꢂWKHꢂVDPHꢂ
VXEVWUDWHVꢂꢌ7DEOHꢂꢆꢍꢉꢂ
7
KXVꢂꢇꢈGHF\OꢈꢁꢈD]DꢈꢇꢈD]RQLDELF\FOR>ꢆꢉꢆꢉꢆ@RFWDQHꢂ
FKORURFKURPDWHꢂꢌ,,,ꢍꢂLVꢂDꢂQHZꢂHIILFLHQWꢂUHDJHQWꢂIRUꢂWKHꢂ
)
RUꢂVXEVWUDWHVꢂ5 5&+2+ꢅꢂVHHꢂ7DEOHꢂꢇꢉꢂ
R[LGDWLRQꢂRIꢂYDULRXVꢂDOFRKROVꢂWRꢂWKHꢂFRUUHVSRQGLQJꢂ
SUHVHQFHꢂRIꢂ$O&O ꢉꢂ$VꢂDꢂUHVXOWꢅꢂWKHꢂFRUUHVSRQGLQJꢂ FDUERQ\OꢂFRPSRXQGVꢂXQGHUꢂPLOGꢂFRQGLWLRQVꢂꢌLQꢂERLOLQJꢂ
FDUERQ\OꢂFRPSRXQGVꢂZHUHꢂLVRODWHGꢂLQꢂJRRGꢂWRꢂH[FHOOHQWꢂ DFHWRQLWULOHꢂLQꢂWKHꢂSUHVHQFHꢂRIꢂ$O&OꢂRUꢂZLWKRXWꢂDꢂVROꢈ
\
]
2
LHOGVꢒꢂIRUꢂH[DPSOHꢅꢂEHQ]RLQꢂZDVꢂWKXVꢂR[LGL]HGꢂWRꢂEHQꢈ
YHQWꢂDWꢂURRPꢂWHPSHUDWXUHꢍꢉꢂ7KHꢂSURSRVHGꢂUHDJHQWꢂLVꢂ
LOꢂLQꢂTXDQWLWDWLYHꢂ\LHOGꢂLQꢂꢑꢄꢂPLQꢂꢌ6FKHPHꢂꢆꢅꢂ7DEOHꢂꢇꢍꢉꢂ VWDEOHꢂDQGꢂHDV\ꢂWRꢂSUHSDUHꢅꢂDQGꢂLWꢂSURYLGHVꢂKLJKꢂ\LHOGVꢂ
RIꢂWKHꢂR[LGDWLRQꢂSURGXFWVꢂDQGꢂVLPSOHꢂSURFHGXUHꢂIRUꢂ
[LGDWLRQꢂRIꢂDOLSKDWLFꢂDOFRKROVꢂUHTXLUHVꢂDꢂORQJHUꢂUHDFꢈ
WLRQꢂWLPHꢅꢂDQGꢂWKHꢂSURGXFWꢂ\LHOGVꢂDUHꢂORZHUꢂWKDQꢂLQꢂꢂ WKHLUꢂLVRODWLRQꢉꢂ
WKHꢂR[LGDWLRQꢂRIꢂEHQ]\OꢂDOFRKROVꢉꢂ7KHꢂSUHVHQFHꢂRIꢂVXFKꢂ
VXEVWLWXHQWVꢂDVꢂ12ꢂRUꢂ0H2ꢂJURXSꢂLQꢂWKHꢂDURPDWLFꢂULQJꢂ
RIꢂEHQ]\OꢂDOFRKROVꢂUHGXFHVꢂWKHꢂUHDFWLRQꢂUDWHꢅꢂSUHVXPꢈ
(
;3(5,0(17$/ꢂ
7
KHꢂ +ꢂDQGꢂ &ꢂ105ꢂVSHFWUDꢂZHUHꢂUHFRUGHGꢂRQꢂꢂ
DEO\ꢂGXHꢂWRꢂSDUWLFLSDWLRQꢂRIꢂWKHVHꢂJURXSVꢂLQꢂFRPSOH[ꢂ
IRUPDWLRQꢂZLWKꢂ$O&Oꢂꢌ7DEOHꢂꢇꢍꢉꢂ
Dꢂ9DULDQꢂVSHFWURPHWHUꢂDWꢂꢃꢄꢄꢂDQGꢂꢐꢎꢂ0+]ꢅꢂUHVSHFꢈ
WLYHO\ꢅꢂXVLQJꢂ'062ꢈG ꢂDVꢂVROYHQWꢂDQGꢂWHWUDPHWK\Oꢈ
VLODQHꢂDVꢂUHIHUHQFHꢉꢂ
&
RPSHWLQJꢂUHDFWLRQVꢂZHUHꢂSHUIRUPHGꢂWRꢂHVWLPDWHꢂ
WKHꢂVHOHFWLYLW\ꢂRIꢂUHDJHQWꢂ,,,ꢂꢌ7DEOHꢂꢆꢍꢉꢂ,QꢂWKHꢂUHDFWLRQꢂ
RIꢂDQꢂHTXLPRODUꢂPL[WXUHꢂRIꢂꢆꢈSKHQ\OHWKDQROꢂDQGꢂEHQ]\Oꢂ
DOFRKROꢂZLWKꢂꢇꢂHTXLYꢂRIꢂ,,,ꢅꢂRQO\ꢂEHQ]\OꢂDOFRKROꢂZDVꢂ
R[LGL]HGꢂWRꢂEHQ]DOGHK\GHꢂꢌ\LHOGꢂꢑꢄꢔꢍꢅꢂZKHUHDVꢂꢂ
ꢆꢈSKHQ\OHWKDQROꢂZDVꢂUHFRYHUHGꢂIURPꢂWKHꢂUHDFWLRQꢂPL[ꢈ
WXUHꢉꢂ7UHDWPHQWꢂRIꢂDꢂꢇꢋꢇꢂPL[WXUHꢂRIꢂEHQ]\OꢂDOFRKROꢂDQGꢂ
GLSKHQ\OPHWKDQROꢂZLWKꢂFRPSRXQGꢂ,,,ꢂꢌꢇꢂHTXLYꢍꢂUHVXOWꢈ
HGꢂLQꢂTXDQWLWDWLYHꢂIRUPDWLRQꢂRIꢂEHQ]RSKHQRQHꢉꢂ,Wꢂ
VKRXOGꢂEHꢂHPSKDVL]HGꢂWKDWꢂLQꢂQRꢂFDVHꢂRYHUR[LGDWLRQꢂRIꢂ
FDUERQ\OꢂFRPSRXQGVꢂWRꢂFDUER[\OLFꢂDFLGVꢂZDVꢂREVHUYHGꢉꢂ
ꢁ
ꢂ'HF\OꢂꢃꢂD]DꢂꢁꢂD]RQLDELF\FOR>ꢄꢅꢄꢅꢄ@RFWDQHꢀ
EURPLGHꢀ ꢉ,,ꢊꢅꢂꢇꢈ%URPRGHFDQHꢅꢂꢆꢁꢉꢄꢂJꢂꢌꢄꢉꢇꢇꢂPPROꢍꢅꢂ
ZDVꢂDGGHGꢂXQGHUꢂVWLUULQJꢂWRꢂDꢂVROXWLRQꢂRIꢂꢇꢆꢉꢄꢂJꢂꢂ
ꢌꢇꢂPPROꢍꢂRIꢂꢇꢅꢁꢈGLD]DELF\FOR>ꢆꢉꢆꢉꢆ@RFWDQHꢂLQꢂꢇꢄꢄꢂPOꢂRIꢂ
DFHWRQHꢉꢂ7KHꢂPL[WXUHꢂZDVꢂKHDWHGꢂIRUꢂꢇꢂKꢂXQGHUꢂUHIOX[ꢂ
DQGꢂFRROHGꢅꢂDQGꢂWKHꢂSUHFLSLWDWHꢂZDVꢂILOWHUHGꢂRIIꢅꢂZDVKHGꢂ
ZLWKꢂGLHWK\OꢂHWKHUꢅꢂDQGꢂGULHGꢉꢂ<LHOGꢂꢆꢀꢉꢎꢂJꢂꢌꢀꢄꢂꢔꢍꢅꢂꢂ
PSꢂꢇꢆꢎ±ꢇꢆꢐƒ&ꢉꢂ +ꢂ105ꢂVSHFWUXPꢅꢂ ꢅꢂSSPꢋꢂꢃꢉꢏꢏ±ꢂ
ꢃꢉꢆꢁꢂPꢂꢌꢇꢆ+ꢍꢅꢂꢇꢉꢁꢀ±ꢄꢉꢑꢆꢂPꢂꢌꢆꢇ+ꢍꢉꢂ
ꢁ
ꢂ'HF\OꢂꢃꢂD]DꢂꢁꢂD]RQLDELF\FOR>ꢄꢅꢄꢅꢄ@RFWDQHꢀ
FKORURFKURPDWHꢀꢉ,,,ꢊꢅꢂꢇꢈ'HF\OꢈꢁꢈD]DꢈꢇꢈD]RQLDELF\FORꢈ
ꢆꢉꢆꢉꢆ@RFWDQHꢂEURPLGHꢂꢌ,,ꢍꢅꢂꢇꢏꢉꢏꢎꢂJꢂꢌꢎꢄꢂPPROꢍꢅꢂZDVꢂ
,
QꢂWKHꢂUHDFWLRQꢂRIꢂFRPSRXQGꢂ,,,ꢂZLWKꢂDQꢂHTXLPRODUꢂ
PL[WXUHꢂRIꢂEHQ]\OꢂDOFRKROꢂDQGꢂEHQ]HQHWKLROꢅꢂEHQ]\Oꢂ
DOFRKROꢂZDVꢂVHOHFWLYHO\ꢂR[LGL]HGꢉꢂ/LNHZVLHꢅꢂRQO\ꢂ
GLSKHQ\OPHWKDQROꢂDQGꢂEHQ]RLQꢂZHUHꢂR[LGL]HGꢂZKHQꢂ
HTXLPRODUꢂGLSKHQ\OPHWKDQRO±EHQ]DOGHK\GHꢂR[LPHꢂDQGꢂ
EHQ]RLQ±ꢃꢈSKHQ\OꢈꢆꢈSURSHQꢈꢇꢈROꢂPL[WXUHVꢅꢂUHVSHFꢈ
WLYHO\ꢅꢂZHUHꢂWUHDWHGꢂZLWKꢂꢇꢂHTXLYꢂRIꢂUHDJHQWꢂ,,,ꢉꢂ
>
GLVVROYHGꢂLQꢂꢎꢄꢂPOꢂRIꢂFKORURIRUPꢅꢂDꢂVROXWLRQꢂRIꢂꢎꢉꢄꢂJꢂ
ꢌꢎꢄꢂPPROꢍꢂRIꢂ&U2ꢂLQꢂꢎꢄꢂPOꢂRIꢂꢏꢂ1ꢂK\GURFKORULFꢂDFLGꢂ
ZDVꢂDGGHGꢂGURSZLVHꢂXQGHUꢂYLJRURXVꢂVWLUULQJꢅꢂDQGꢂWKHꢂ
PL[WXUHꢂZDVꢂYLJRURXVO\ꢂVWLUUHGꢂIRUꢂꢆꢄꢂPLQꢂDWꢂURRPꢂ
WHPSHUDWXUHꢉꢂ7KHꢂRUDQJHꢂSUHFLSLWDWHꢂZDVꢂILOWHUHGꢂRIIꢅꢂ
ZDVKHGꢂZLWKꢂFROGꢂGLVWLOOHGꢂZDWHUꢂꢌꢆîꢎꢄꢂPOꢍꢅꢂDQGꢂGULHGꢂ
LQꢂDꢂYDFXXPꢂGHVLFFDWRUꢂRYHUꢂFDOFLXPꢂFKORULGHꢉꢂ<LHOGꢂ
:HꢂDOVRꢂSHUIRUPHGꢂR[LGDWLRQꢂRIꢂDOFRKROVꢂWRꢂFDUꢈ
ERQ\OꢂFRPSRXQGVꢂZLWKꢂꢇꢈGHF\OꢈꢁꢈD]DꢈꢇꢈD]RQLDELF\FORꢈ
>ꢆꢉꢆꢉꢆ@RFWDQHꢂFKORURFKURPDWHꢂꢌ,,,ꢍꢂXQGHUꢂVROYHQWꢈIUHHꢂ ꢇꢏꢉꢇꢁꢂJꢂꢌꢀꢃꢔꢍꢒꢂRQꢂKHDWLQJꢂWRꢂꢇꢆꢏ±ꢇꢆꢀƒ&ꢂFRPSRXQGꢂ
FRQGLWLRQVꢉꢂ7KHꢂUHDFWLRQVꢂZHUHꢂFDUULHGꢂRXWꢂE\ꢂJULQGLQJꢂ ,,,ꢂGHFRPSRVHVꢂWRꢂJLYHꢂDꢂGDUNꢂEURZQꢂPDWHULDOꢉꢂ +ꢂ105ꢂ
DꢂPL[WXUHꢂRIꢂDQꢂDOFRKROꢂDQGꢂFRPSRXQGꢂ,,,ꢂLQꢂDꢂPRUWDUꢂ VSHFWUXPꢅꢂ ꢅꢂSSPꢋꢂꢃꢉꢀꢁ±ꢃꢉꢆꢁꢂPꢂꢌꢇꢆ+ꢍꢅꢂꢇꢉꢏꢏ±ꢄꢉꢀꢁꢂPꢂ
DWꢂURRPꢂWHPSHUDWXUHꢉꢂ$VꢂDꢂUHVXOWꢅꢂWKHꢂFRUUHVSRQGLQJꢂ ꢌꢆꢇ+ꢍꢉꢂ &ꢂ105ꢂVSHFWUXPꢅꢂ ꢅꢂSSPꢋꢂꢃꢆꢉꢏꢏꢅꢂꢃꢄꢉꢆꢐꢅꢂ
FDUERQ\OꢂFRPSRXQGVꢂZHUHꢂREWDLQHGꢂLQꢂKLJKꢂ\LHOGVꢂLQꢂꢂ ꢃꢄꢅꢇꢎꢅꢂꢃꢄꢉꢄꢎꢅꢂꢆꢑꢉꢀꢀꢅꢂꢆꢑꢉꢀꢆꢅꢂꢆꢐꢉꢇꢀꢅꢂꢆꢏꢉꢑꢆꢅꢂꢆꢃꢉꢁꢀꢅꢂꢆꢆꢉꢏꢑꢅꢂ
DꢂVKRUWꢂWLPHꢉꢂ)RUꢂLQVWDQFHꢅꢂEHQ]RLQꢂZDVꢂTXDQWLWDWLYHO\ꢂ ꢆꢆꢉꢎꢄꢅꢂꢇꢎꢉꢃꢃꢉꢂ)RXQGꢅꢂꢔꢋꢂ&ꢂꢁꢑꢉꢆꢑꢒꢂ+ꢂꢀꢉꢐꢃꢒꢂ1ꢂꢐꢉꢆꢀꢉꢂ
FRQYHUWHGꢂLQWRꢂEHQ]LOꢂLQꢂꢎꢂPLQꢂꢌ7DEOHꢂꢇꢍꢉꢂ$VꢂFRPSDUHGꢂ & + 1 Â&U2&Oꢉꢂ&DOFXODWHGꢅꢂꢔꢋꢂ&ꢂꢁꢑꢉꢁꢆꢒꢂ+ꢂꢀꢉꢁꢑꢒꢂꢂ
WRꢂWKHꢂR[LGDWLRQꢂLQꢂERLOLQJꢂDFHWRQLWULOHꢅꢂWKHꢂUHDFWLRQꢂ 1ꢂꢐꢉꢆꢄꢉꢂꢂ
XQGHUꢂVROYHQWꢈIUHHꢂFRQGLWLRQVꢂRFFXUVꢂDWꢂDꢂPXFKꢂKLJKHUꢂ
UDWHꢂDQGꢂHQVXUHVꢂKLJKHUꢂ\LHOGVꢂRIꢂWKHꢂSURGXFWVꢉꢂ,QꢂDGꢈ
2[LGDWLRQꢀ RIꢀ DOFRKROVꢀ ZLWKꢀ ꢁꢂGHF\OꢂꢃꢂD]Dꢂꢁꢂ
D]RQLDELF\FOR>ꢄꢅꢄꢅꢄ@RFWDQHꢀ FKORURFKURPDWHꢀ ꢉ,,,ꢊꢀ LQꢀ
GLWLRQꢅꢂWKHꢂLVRODWLRQꢂSURFHGXUHꢂLVꢂPXFKꢂVLPSOHUꢅꢂDQGꢂQRꢂ ERLOLQJꢀ DFHWRQLWULOHꢀ ꢉJHQHUDOꢀ SURFHGXUHꢊꢅꢂ&RPSRXQGꢂ
O&OꢂLVꢂQHFHVVDU\ꢉꢂ(VWLPDWLRQꢂRIꢂWKHꢂVHOHFWLYLW\ꢂLQꢂWKHꢂ ,,,ꢅꢂꢄꢉꢃꢑꢂJꢂꢌꢇꢂPPROꢍꢅꢂDQGꢂ$O&O ꢅꢂꢏꢎꢉꢇꢂPJꢂꢌꢄꢉꢇꢏꢂPPROꢍꢅꢂ
R[LGDWLRQꢂRIꢂDOFRKROVꢂZLWKRXWꢂDꢂVROYHQWꢂE\ꢂWKHꢂFRPꢈ
ZHUHꢂDGGHGꢂWRꢂDꢂVROXWLRQꢂRIꢂꢇꢂPPROꢂRIꢂWKHꢂFRUUHVSRQGꢈ
$
5
866,$1ꢂꢂ-2851$/ꢂꢂ2)ꢂꢂ25*$1,&ꢂꢂ&+(0,675<ꢂꢂꢂ9ROꢉꢂꢂꢁꢆꢂꢂꢂ1Rꢉꢂꢂꢏꢂꢂꢂꢆꢄꢄꢏꢂ

ꢀ
ꢁꢏꢂ
+$-,3285ꢂꢂHWꢂDOꢉ
7DEOHꢀꢁꢅꢂ2[LGDWLRQꢂRIꢂDOFRKROVꢂZLWKꢂꢇꢈGHF\OꢈꢁꢈD]DꢈꢇꢈD]RQLDELF\FOR>ꢆꢉꢆꢉꢆ@RFWDQHꢂFKORURFKURPDWHꢂꢌ,,,ꢍꢂLQꢂERLOLQJꢂDFHWRQLWULOHꢂ
LQꢂWKHꢂSUHVHQFHꢂRIꢂ$O&OꢂDQGꢂXQGHUꢂVROYHQWꢈIUHHꢂFRQGLWLRQVꢂ
5
HDFWLRQꢂLQꢂDFHWRQLWULOHꢂ
5HDFWLRQꢂZLWKRXWꢂDꢂVROYHQWꢂ
$OFRKROꢂ
WLPHꢅꢂKꢂ
\LHOGꢅꢂꢔꢂ
WLPHꢅꢂPLQꢂ
\LHOGꢅꢂꢔꢂ
%
HQ]\OꢂDOFRKROꢂ
ꢄꢉꢎꢂ
ꢇꢉꢎꢂ
ꢇꢉꢎꢂ
ꢆꢉꢄꢂ
ꢆꢉꢄꢂ
ꢇꢉꢄꢂ
ꢇꢉꢎꢂ
ꢇꢉꢀꢂ
ꢄꢉꢀꢂ
ꢇꢉꢀꢂ
ꢇꢉꢄꢂ
ꢇꢉꢄꢂ
ꢇꢉꢎꢂ
ꢆꢉꢄꢂ
ꢇꢉꢃꢂ
ꢇꢉꢎꢂ
ꢇꢉꢁꢂ
ꢆꢉꢃꢂ
ꢇꢉꢄꢂ
ꢆꢉꢎꢂ
ꢆꢉꢎꢂ
ꢆꢉꢎꢂ
ꢆꢉꢆꢂ
ꢆꢉꢄꢂ
ꢆꢉꢎꢂ
ꢇꢉꢎꢂ
ꢆꢉꢄꢂ
ꢆꢉꢄꢂ
ꢇꢉꢆꢂ
ꢆꢉꢄꢂ
ꢆꢉꢆꢂ
ꢆꢉꢃꢂ
ꢆꢉꢄꢂ
ꢆꢉꢄꢂ
ꢆꢉꢄꢂ
ꢆꢉꢆꢂ
ꢆꢉꢀꢂ
ꢆꢉꢎꢂ
ꢑꢀꢂ
ꢀꢎꢂ
ꢑꢎꢂ
ꢑꢀꢂ
ꢑꢇꢂ
ꢑꢀꢂ
ꢑꢀꢂ
ꢑꢑꢂ
ꢇꢄꢄꢄꢂ
ꢑꢑꢂ
ꢑꢎꢂ
ꢑꢁꢂ
ꢑꢃꢂ
ꢑꢁꢂ
ꢑꢏꢂ
ꢇꢄꢄꢄꢂ
ꢑꢑꢂ
ꢑꢐꢂ
ꢑꢀꢂ
ꢀꢀꢂ
ꢑꢄꢂ
ꢀꢑꢂ
ꢑꢁꢂ
ꢑꢇꢂ
ꢑꢃꢂ
ꢑꢏꢂ
ꢀꢑꢂ
ꢑꢄꢂ
ꢑꢁꢂ
ꢑꢄꢂ
ꢑꢁꢂ
ꢑꢆꢂ
ꢑꢇꢂ
ꢑꢏꢂ
ꢑꢆꢂ
ꢑꢇꢂ
ꢑꢁꢂ
ꢑꢏꢂ
ꢄꢏꢉꢄꢂ
ꢇꢐꢉꢄꢂ
ꢄꢆꢉꢄꢂ
ꢄꢃꢉꢄꢂ
ꢄꢏꢉꢄꢂ
ꢄꢁꢉꢄꢂ
ꢄꢆꢉꢄꢂ
ꢄꢆꢉꢄꢂ
ꢄꢃꢉꢄꢂ
ꢄꢎꢉꢄꢂ
ꢄꢐꢉꢄꢂ
ꢄꢁꢉꢎꢂ
ꢄꢁꢉꢎꢂ
ꢄꢎꢉꢄꢂ
ꢄꢇꢉꢎꢂ
ꢄꢎꢉꢄꢂ
ꢄꢃꢉꢄꢂ
ꢄꢁꢉꢄꢂ
ꢄꢇꢉꢎꢂ
ꢄꢁꢉꢎꢂ
ꢄꢁꢉꢎꢂ
ꢆꢄꢉꢄꢂ
ꢄꢃꢉꢄꢂ
ꢄꢁꢉꢄꢂ
ꢄꢁꢉꢎꢂ
ꢆꢉꢂ
ꢑꢎꢂ
ꢑꢀꢂ
ꢑꢄꢂ
ꢑꢀꢂ
ꢑꢁꢂ
ꢑꢎꢂ
ꢑꢑꢂ
ꢑꢑꢂ
ꢇꢄꢄꢂ
ꢑꢑꢂ
ꢑꢎꢂ
ꢀꢀꢂ
ꢑꢎꢂ
ꢑꢑꢂ
ꢀꢎꢂ
ꢇꢄꢄꢄꢂ
ꢑꢃꢂ
ꢑꢄꢂ
ꢑꢃꢂ
ꢐꢎꢂ
ꢐꢀꢂ
ꢑꢆꢂ
ꢀꢑꢂ
ꢀꢀꢂ
ꢀꢐꢂ
ꢑꢆꢂ
ꢐꢎꢂ
ꢀꢀꢂ
ꢑꢀꢂ
ꢀꢀꢂ
ꢀꢎꢂ
ꢑꢁꢂ
ꢀꢀꢂ
ꢀꢎꢂ
ꢀꢎꢂ
ꢑꢆꢂ
ꢑꢄꢂ
ꢑꢆꢂ
ꢁ
ꢈ1LWUREHQ]\OꢂDOFRKROꢂ
ꢃꢅꢁꢈ'LPHWKR[\EHQ]\OꢂDOFRKROꢂ
ꢇꢈꢌꢁꢈ%LSKHQ\O\OꢍHWKDQROꢂ
ꢆꢈ3\ULG\OPHWKDQROꢂ
ꢇꢈ3KHQ\OHWKDQROꢂ
ꢁ
ꢈ0HWKR[\EHQ]\OꢂDOFRKROꢂ
ꢆꢈ0HWKR[\EHQ]\OꢂDOFRKROꢂ
LSKHQ\OPHWKDQROꢂ
ꢃꢈ0HWKR[\EHQ]\OꢂDOFRKROꢂ
ꢈ&KORUREHQ]\OꢂDOFRKROꢂ
'
ꢁ
ꢆꢈ&KORUREHQ]\OꢂDOFRKROꢂ
ꢇꢅꢆꢈ'LSKHQ\OHWKDQROꢂ
ꢇꢈꢌꢁꢈ%URPRSKHQ\OꢍHWKDQROꢂ
ꢇꢈꢌꢁꢈ&KORURSKHQ\OꢍHWKDQROꢂ
%
HQ]RLQꢂ
ꢆꢅꢃꢈ'LPHWKR[\EHQ]\OꢂDOFRKROꢂ
\FORKH[DQROꢂ
&
ꢇꢅꢆꢅꢃꢅꢁꢈ7HWUDK\GURQDSKWKDOHQꢈꢇꢈROꢂ
Qꢈ+HSWDQROꢂ
Qꢈ3HQWDQROꢂ
/
ꢈ0HQWKROꢂ
ꢇꢈ,QGDQROꢂ
ꢑꢈ)OXRUHQROꢂ
WUDQVꢈꢁꢈ'HF\OF\FORKH[DQROꢂ
ꢆꢈ1DSKWK\OPHWKDQROꢂ
ꢆꢈ3KHQ\OHWKDQROꢂ
ꢆꢄꢉꢄꢂ
ꢄꢁꢉꢄꢂ
ꢄꢇꢉꢎꢂ
ꢆꢄꢉꢄꢂ
ꢇꢎꢉꢄꢂ
ꢇꢎꢉꢄꢂ
ꢇꢄꢉꢄꢂ
ꢆꢄꢉꢄꢂ
ꢇꢎꢉꢄꢂ
ꢄꢀꢉꢄꢂ
ꢇꢄꢉꢄꢂ
ꢆꢄꢉꢄꢂ
ꢃꢈ0HWK\OF\FORKH[DQROꢂ
ꢇꢈꢌꢁꢈ0HWK\OSKHQ\OꢍHWKDQROꢂ
ꢃꢈ3KHQ\OSURSDQꢈꢇꢈROꢂ
&
\FORRFWDQROꢂ
$
*
GDPDQWDQꢈꢆꢈROꢂ
HUDQLROꢂ
ꢃꢈ3KHQ\OꢈꢆꢈSURSHQꢈꢇꢈROꢂ
ꢆꢈ1LWUREHQ]\OꢂDOFRKROꢂ
ꢆꢈ+\GUR[\ꢈꢎꢈQLWUREHQ]\OꢂDOFRKROꢂ
ꢌꢁꢈ&KORURSKHQ\OꢍSKHQ\OPHWKDQROꢂ
ꢇꢈꢌꢁꢈ&KORURSKHQ\OꢍHWKDQROꢂ
ꢂ7KHꢂSURGXFWVꢂZHUHꢂLGHQWLILHGꢂE\ꢂFRPSDULQJꢂZLWKꢂDXWKHQWLFꢂVDPSOHVꢂꢌ,5ꢅꢂ105ꢅꢂDQGꢂ7/&ꢂGDWDꢍꢂ>ꢇꢇ±ꢇꢃ@ꢉꢂꢂ
ꢂ<LHOGꢂRIꢂWKHꢂSXULILHGꢂSURGXFWꢉꢂ
5
866,$1ꢂꢂ-2851$/ꢂꢂ2)ꢂꢂ25*$1,&ꢂꢂ&+(0,675<ꢂꢂꢂ9ROꢉꢂꢂꢁꢆꢂꢂꢂ1Rꢉꢂꢂꢏꢂꢂꢂꢆꢄꢄꢏꢂ

2
;,'$7,21ꢂꢂ2)ꢂꢂ$/&2+2/6ꢂꢂ:,7+ꢂꢂꢇꢈ'(&</ꢈꢁꢈ$=$ꢈꢇꢈ$=21,$%,&<&/2>ꢆꢉꢆꢉꢆ@2&7$1(ꢂ
ꢀꢁꢐꢂ
7DEOHꢀꢄꢅꢂ&RPSHWLQJꢂR[LGDWLRQꢂRIꢂDOFRKROVꢂZLWKꢂꢇꢈGHF\OꢈꢁꢈD]DꢈꢇꢈD]RQLDELF\FOR>ꢆꢉꢆꢉꢆ@RFWDQHꢂFKORURFKURPDWHꢂꢌ,,,ꢍꢂLQꢂERLOLQJꢂ
DFHWRQLWULOHꢂLQꢂWKHꢂSUHVHQFHꢂRIꢂ$O&OꢂDQGꢂXQGHUꢂVROYHQWꢈIUHHꢂFRQGLWLRQVꢂ
5
HDFWLRQꢂLQꢂDFHWRQLWULOHꢂ
5HDFWLRQꢂZLWKRXWꢂDꢂVROYHQWꢂ
6
XEVWUDWHꢂ
3URGXFWꢂ
3K&+2ꢂ
WLPHꢅꢂKꢂ
ꢄꢃꢄꢂ
\LHOGꢅꢂꢔꢂ
ꢄꢑꢄꢂ
WLPHꢅꢂPLQꢂ
ꢇꢄꢂ
\LHOGꢅꢂꢔꢂ
ꢄꢑꢎꢂ
3
3
3
3
3
K&+&+2+ꢂꢕꢂ3K&+2+ꢂ
K&+2+3Kꢂꢕꢂ3K&+ 2+ꢂ
K60Hꢂꢕꢂ3K&+2+ꢂ
3K&23Kꢂ
3K&+2ꢂ
3K&23Kꢂ
ꢄꢃꢄꢂ
ꢄꢃꢄꢂ
ꢇꢀꢄꢂ
ꢄꢑꢄꢂ
ꢇꢄꢄꢂ
ꢄꢑꢄꢂ
ꢄꢑꢆꢂ
ꢄꢑꢎꢂ
ꢄꢎꢂ
ꢇꢄꢂ
ꢇꢄꢂ
ꢇꢄꢂ
ꢇꢄꢄꢂ
ꢄꢑꢎꢂ
ꢄꢑꢎꢂ
ꢄꢑꢎꢂ
K&+2+3Kꢂꢕꢂ3K&+ 12+ꢂ
K&+2+&23Kꢂꢕꢂ3K&+ &+&+ 2+ꢂ 3K&2&23Kꢂ
LQJꢂDOFRKROꢂLQꢂꢎꢂPOꢂRIꢂDFHWRQLWULOHꢅꢂDQGꢂWKHꢂPL[WXUHꢂZDVꢂ ꢂꢂꢃꢉꢂ/H\ꢅꢂ 6ꢉ9ꢉꢅꢂ 1RUPDQQꢅꢂ -ꢉꢅꢂ *ULIILWKꢅꢂ :ꢉ3ꢉꢅꢂ DQGꢂ 0DUVꢈꢂ
KHDWHGꢂXQGHUꢂUHIOX[ꢂXQWLOꢂWKHꢂLQLWLDOꢂDOFRKROꢂGLVDSSHDUHGꢂ
GHQꢅꢂ6ꢉ3ꢉꢅꢂ6\QWKHVLVꢅꢂꢇꢑꢑꢁꢅꢂSꢉꢂꢏꢃꢑꢉꢂ
ꢌDFFRUGLQJꢂWRꢂWKHꢂ7/&ꢂGDWDꢒꢂF\FORKH[DQH±HWK\OꢂDFHWDWHꢅꢂ ꢂꢂꢁꢉꢂ+XGOLFN\ꢅꢂ 0ꢉꢅꢂ 2[LGDWLRQꢀ LQꢀ 2UJDQLFꢀ &KHPLVWU\ꢅꢂ
ꢑꢋꢇꢍꢉꢂ:KHQꢂWKHꢂUHDFWLRQꢂZDVꢂFRPSOHWHꢅꢂWKHꢂPL[WXUHꢂ
:DVKLQJWRQꢅꢂ'&ꢋꢂ$Pꢉꢂ&KHPꢉꢂ6RFꢉꢅꢂꢇꢑꢑꢄꢉꢂ
ZDVꢂFRROHGꢂWRꢂURRPꢂWHPSHUDWXUHꢂDQGꢂILOWHUHGꢂWKURXJKꢂꢂ ꢂꢂꢎꢉꢂ6WHYHQVꢅꢂ 5ꢉ9ꢉꢅꢂ &KDSPDQꢅꢂ .ꢉ7ꢉꢅꢂ DQGꢂ :DOWHUꢅꢂ +ꢉ1ꢉꢅꢂꢂ
DꢂVPDOOꢂOD\HUꢂRIꢂVLOLFDꢂJHOꢅꢂWKHꢂVRUEHQWꢂZDVꢂZDVKHGꢂZLWKꢂ
-ꢍꢀ2UJꢍꢀ&KHPꢉꢅꢂꢇꢑꢀꢄꢅꢂYROꢉꢂꢁꢎꢅꢂSꢉꢂꢆꢄꢃꢄꢉꢂ
ꢇꢎꢂPOꢂRIꢂDFHWRQLWULOHꢅꢂWKHꢂILOWUDWHꢂZDVꢂFRPELQHGꢂZLWKꢂ ꢂꢂꢏꢉꢂ+ROXPꢅꢂ-ꢉ5ꢉꢅꢂ-ꢍꢀ2UJꢍꢀ&KHPꢉꢅꢂꢇꢑꢏꢇꢅꢂYROꢉꢂꢆꢏꢅꢂSꢉꢂꢁꢀꢇꢁꢉꢂ
ꢂ
ꢂ
ꢂ
WKHꢂZDVKLQJVꢂDQGꢂHYDSRUDWHGꢅꢂDQGꢂWKHꢂUHVLGXHꢂZDVꢂ
SXULILHGꢂE\ꢂFROXPQꢂFKURPDWRJUDSK\ꢂRQꢂVLOLFDꢂJHOꢂXVLQJꢂ
HWK\OꢂDFHWDWH±KH[DQHꢂꢌꢇꢄꢋꢑꢄꢍꢂDVꢂHOXHQWꢉꢂ7KHꢂ\LHOGVꢂRIꢂ
SXUHꢂFDUERQ\OꢂFRPSRXQGVꢂZHUHꢂꢀꢎ±ꢇꢄꢄꢔꢂꢌ7DEOHꢂꢇꢍꢉꢂ
ꢂꢂꢐꢉꢂ/HHꢅꢂ'ꢉ*ꢉꢅꢂ-ꢍꢀ2UJꢍꢀ&KHPꢉꢅꢂꢇꢑꢐꢄꢅꢂYROꢉꢂꢃꢎꢅꢂSꢉꢂꢃꢎꢀꢑꢉꢂ
ꢂꢂꢀꢉꢂ+LJKHWꢅꢂ5ꢉ-ꢉꢅꢂDQGꢂ:LOGPDQꢅꢂ:ꢉ&ꢉꢅꢂ-ꢍꢀ $Pꢍꢀ &KHPꢍꢀ 6RFꢉꢅꢂ
ꢂ
ꢇꢑꢎꢎꢅꢂYROꢉꢂꢐꢐꢅꢂSꢉꢂꢁꢃꢑꢑꢉꢂ
ꢂꢂꢑꢉꢂ5DKPDQꢅꢂ0ꢉꢂDQGꢂ5RFHNꢅꢂ-ꢉꢅꢂ-ꢍꢀ $Pꢍꢀ &KHPꢍꢀ 6RFꢉꢅꢂꢇꢑꢐꢇꢅꢂ
YROꢉꢂꢑꢃꢅꢂSꢉꢂꢎꢁꢎꢎꢉꢂꢂ
ꢂD]RQLDELF\FOR>ꢄꢅꢄꢅꢄ@RFWDQHꢀ FKORURFKURPDWHꢀ ꢉ,,,ꢊꢀ ꢇꢄꢉꢂ1DYDꢅꢂ3ꢉ0ꢉꢂDQGꢂ7UDKQRYVN\ꢅꢂ:ꢉ6ꢉꢅꢂ-ꢍꢀ$Pꢍꢀ&KHPꢍꢀ6RFꢉꢅꢂ
ꢂ
2
[LGDWLRQꢀ RIꢀEHQ]\OꢀDOFRKROꢀZLWKꢀꢁꢂGHF\OꢂꢃꢂD]Dꢂ
ꢁ
XQGHUꢀ VROYHQWꢂIUHHꢀ FRQGLWLRQVꢅꢂ$ꢂPL[WXUHꢂRIꢂꢄꢉꢃꢑꢂJꢂꢂ
ꢌꢇꢂPPROꢍꢂRIꢂꢇꢈGHF\OꢈꢁꢈD]DꢈꢇꢈD]RQLDELF\FOR>ꢆꢉꢆꢉꢆ@ꢈ
RFWDQHꢂFKORURFKURPDWHꢂꢌ,,,ꢍꢂDQGꢂꢄꢉꢇꢇꢂJꢂꢌꢇꢂPPROꢍꢂRIꢂ
ꢂ
ꢇꢑꢐꢄꢅꢂYROꢉꢂꢑꢆꢅꢂSꢉꢂꢇꢇꢆꢄꢉꢂ
ꢇꢇꢉꢂ0DQJHUꢅꢂ)ꢉ0ꢉꢂDQGꢂ/HHꢅꢂ&ꢉꢅꢂ7HWUDKHGURQꢀ /HWWꢉꢅꢂꢇꢑꢀꢇꢅꢂꢂ
YROꢉꢂꢆꢆꢅꢂSꢉꢂꢇꢏꢎꢏꢉꢂ
ꢂ
EHQ]\OꢂDOFRKROꢂZDVꢂJURXQGꢂLQꢂDꢂPRUWDUꢂDWꢂURRPꢂWHPꢈ ꢇꢆꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢅꢂ0DOODNSRXUꢅꢂ6ꢉ(ꢉꢅꢂDQGꢂ,PDQ]DGHKꢅꢂ*ꢉꢅꢂꢂ
SHUDWXUHꢉꢂ7KHꢂSURJUHVVꢂRIꢂWKHꢂUHDFWLRQꢂZDVꢂPRQLWRUHGꢂ
-ꢍꢀ&KHPꢍꢀ5HVꢍꢁꢀ6\QRSꢉꢅꢂꢇꢑꢑꢑꢅꢂSꢉꢂꢆꢆꢀꢉꢂꢂ
E\ꢂ7/&ꢅꢂIROORZLQJꢂGLVDSSHDUDQFHꢂRIꢂWKHꢂLQLWLDOꢂDOFRKROꢉꢂ ꢇꢃꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢅꢂ0DOODNSRXUꢅꢂ6ꢉ(ꢉꢅꢂDQGꢂ$GLELꢅꢂ+ꢉꢅꢂ&KHPꢍꢀ
KHQꢂWKHꢂUHDFWLRQꢂZDVꢂFRPSOHWHꢅꢂWKHꢂPL[WXUHꢂZDVꢂ
/HWWꢉꢅꢂꢆꢄꢄꢄꢅꢂSꢉꢂꢁꢏꢄꢉꢂꢂ
WUHDWHGꢂZLWKꢂF\FORKH[DQHꢂDQGꢂILOWHUHGꢉꢂ7KHꢂILOWUDWHꢂZDVꢂ ꢇꢁꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢅꢂ0DOODNSRXUꢅꢂ6ꢉ(ꢉꢅꢂDQGꢂ$IURXVKHKꢅꢂ$ꢉꢅꢂ
ꢂ
:
ꢀ
HYDSRUDWHGꢂXQGHUꢂUHGXFHGꢂSUHVVXUHꢅꢂDQGꢂWKHꢂFUXGHꢂ
SURGXFWꢂꢌEHQ]DOGHK\GHꢍꢂZDVꢂSXULILHGꢂE\ꢂIODVKꢂFKURPDꢈ
WRJUDSK\ꢂRQꢂVLOLFDꢂJHOꢂXVLQJꢂHWK\OꢂDFHWDWH±KH[DQHꢂ
ꢂ
7HWUDKHGURQꢅꢂꢇꢑꢑꢑꢅꢂYROꢉꢂꢎꢎꢅꢂSꢉꢂꢆꢃꢇꢇꢉꢂꢂ
ꢇꢎꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢂDQGꢂ,VODPLꢅꢂ)ꢉꢅꢂ,QGLDQꢀ-ꢍꢀ&KHPꢍꢁꢀ6HFWꢍꢀ%ꢅꢂ
ꢇꢑꢑꢑꢅꢂYROꢉꢂꢃꢀꢅꢂSꢉꢂꢁꢏꢇꢉꢂꢂ
ꢂ
ꢌꢇꢄꢋꢑꢄꢍꢂDVꢂHOXHQWꢉꢂ7KHꢂRWKHUꢂDOFRKROVꢂZHUHꢂR[LGL]HGꢂLQꢂ ꢇꢏꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢅꢂ0DOODNSRXUꢅꢂ6ꢉ(ꢉꢅꢂDQGꢂ,PDQ]DGHKꢅꢂ*ꢉꢅꢂ
DꢂVLPLODUꢂZD\ꢂꢌ7DEOHꢂꢇꢍꢉꢂ
&KHPꢍꢀ/HWWꢉꢅꢂꢇꢑꢑꢑꢅꢂSꢉꢂꢑꢑꢉꢂꢂ
ꢇꢐꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢂDQGꢂ+DQWHK]DGHKꢅꢂ0ꢉꢅꢂ-ꢍꢀ 2UJꢍꢀ &KHPꢉꢅꢂ
ꢂ
7
KHꢂDXWKRUVꢂJUDWHIXOO\ꢂDFNQRZOHGJHꢂILQDQFLDOꢂVXSꢈ
ꢂ
ꢇꢑꢑꢑꢅꢂYROꢉꢂꢏꢁꢅꢂSꢉꢂꢀꢁꢐꢎꢉꢂꢂ
SRUWꢂUHFHLYHGꢂIRUꢂWKLVꢂVWXG\ꢂIURPꢂWKHꢂ,VIDKDQꢂ8QLYHUVLW\ꢂ
RIꢂ7HFKQRORJ\ꢂꢌ,87ꢅꢂ,5ꢂ,UDQꢍꢅꢂ1DWLRQDOꢂ,QVWLWXWHVꢂRIꢂ
ꢇꢀꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢅꢂ0DOODNSRXUꢅꢂ6ꢉ(ꢉꢅꢂDQGꢂ%DFNQHMDGꢅꢂ+ꢉꢅꢂ
6\QWKꢍꢀ&RPPXQꢉꢅꢂꢆꢄꢄꢄꢅꢂYROꢉꢂꢃꢄꢅꢂSꢉꢂꢃꢀꢎꢎꢉꢂꢂ
ꢇꢑꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢅꢂ0DOODNSRXUꢅꢂ6ꢉ(ꢉꢅꢂDQGꢂ$IURXVKHKꢅꢂ$ꢉꢅꢂ
3KRVSKRUXVꢁꢀ6XOIXUꢁꢀ6LOLFRQꢅꢂꢆꢄꢄꢄꢅꢂYROꢉꢂꢇꢏꢄꢅꢂSꢉꢂꢏꢐꢉꢂꢂ
ꢆꢄꢉꢂ+DMLSRXUꢅꢂ $ꢉ5ꢉꢅꢂ 0DOODNSRXUꢅꢂ 6ꢉ(ꢉꢅꢂ DQGꢂ .KRHHꢅꢂ 6ꢉꢅꢂ
6\QOHWWꢅꢂꢆꢄꢄꢄꢅꢂSꢉꢂꢐꢁꢄꢉꢂꢂ
ꢇꢉꢂ)LHVHUꢅꢂ /ꢉꢂ DQGꢂ )LHVHUꢅꢂ )ꢉ0ꢉꢅꢂ 5HDJHQWVꢀ IRUꢀ 2UJDQLFꢀ ꢆꢇꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢅꢂ0DOODNSRXUꢅꢂ6ꢉ(ꢉꢅꢂDQGꢂ.KRHHꢅꢂ6ꢉꢅꢂ&KHPꢍꢀ
6\QWKHVLVꢅꢂ1HZꢂ<RUNꢋꢂ:LOH\ꢅꢂꢇꢑꢏꢐꢅꢂYROꢉꢂꢇꢉꢂ
/HWWꢉꢅꢂꢆꢄꢄꢄꢅꢂSꢉꢂꢇꢆꢄꢉꢂꢂ
ꢆꢉꢂ6KHOGRQꢅꢂ5ꢉ$ꢉꢂDQGꢂ.RFKLꢅꢂ-ꢉ.ꢉꢅꢂ0HWDOꢊ&DWDO\]HGꢀ2[LGDꢊ
ꢆꢆꢉꢂ+DMLSRXUꢅꢂ $ꢉ5ꢉꢅꢂ %DOWRUNꢅꢂ ,ꢉ0ꢉꢅꢂ 1LNEDJKDWꢅꢂ .ꢉꢅꢂ DQGꢂ
WLRQꢀRIꢀ2UJDQLFꢀ&RPSRXQGVꢅꢂ1HZꢂ<RUNꢋꢂ$FDGHPLFꢅꢂꢇꢑꢀꢇꢉꢂ
,PDQ]DGHKꢅꢂ*ꢉꢅꢂ6\QWKꢍꢀ&RPPXQꢉꢅꢂꢇꢑꢑꢑꢅꢂYROꢉꢂꢆꢑꢅꢂSꢉꢂꢇꢏꢑꢐꢉꢂ
ꢂ
+
HDOWKꢅꢂ86$ꢂꢌ*UDQWꢂ*0ꢂꢃꢃꢇꢃꢀꢍꢅꢂDQGꢂ&HQWHUꢂRIꢂ([FHOꢈ
OHQF\ꢂLQꢂ&KHPLVWU\ꢂ5HVHDUFKꢂꢌ,87ꢍꢉꢂ
ꢂ
5()(5(1&(6ꢂ
ꢂ
ꢀ
ꢀ
ꢀ
ꢂ
5
866,$1ꢂꢂ-2851$/ꢂꢂ2)ꢂꢂ25*$1,&ꢂꢂ&+(0,675<ꢂꢂꢂ9ROꢉꢂꢂꢁꢆꢂꢂꢂ1Rꢉꢂꢂꢏꢂꢂꢂꢆꢄꢄꢏꢂ

ꢀ
ꢁꢀꢂ
+$-,3285ꢂꢂHWꢂDOꢉ
ꢆꢃꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢂDQGꢂ0DKERXENKDKꢅꢂ1ꢉꢅꢂ-ꢍꢀ &KHPꢍꢀ 5HVꢍꢁꢀ ꢆꢑꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢅꢂ%DOWRUNꢅꢂ,ꢉ0ꢉꢅꢂDQGꢂ.LDQIDUꢅꢂ*ꢉꢅꢂ%XOOꢍꢀ
6\QRSꢉꢅꢂꢇꢑꢑꢀꢅꢂSꢉꢂꢇꢆꢆꢉꢂꢂ &KHPꢍꢀ6RFꢍꢀ-SQꢉꢅꢂꢇꢑꢑꢀꢅꢂYROꢉꢂꢐꢇꢅꢂSꢉꢂꢆꢏꢎꢎꢉꢂꢂ
ꢆꢁꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢅꢂ0DOODNSRXUꢅꢂ6ꢉ(ꢉꢅꢂDQGꢂ$GLELꢅꢂ+ꢉꢅꢂ&KHPꢍꢀ ꢃꢄꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢅꢂ%DOWRUNꢅꢂ,ꢉ0ꢉꢅꢂDQGꢂ.LDQIDUꢅꢂ*ꢉꢅꢂ,QGLDQꢀ-ꢍꢀ
/HWWꢉꢅꢂꢆꢄꢄꢄꢅꢂSꢉꢂꢁꢏꢄꢉꢂꢂ &KHPꢍꢁꢀ6HFWꢍꢀ%ꢅꢂꢇꢑꢑꢀꢅꢂYROꢉꢂꢃꢐꢅꢂSꢉꢂꢏꢄꢐꢉꢂꢂ
ꢆꢎꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢅꢂ0DOODNSRXUꢅꢂ6ꢉ(ꢉꢅꢂDQGꢂ.KRHHꢅꢂ6ꢉꢅꢂ&KHPꢍꢀ ꢃꢇꢉꢂ+DMLSRXUꢅꢂ $ꢉ5ꢉꢂ DQGꢂ 0DKERRENKDKꢅꢂ 1ꢉꢅꢂ 2UJꢍꢀ 3UHSꢍꢀ
/HWWꢉꢅꢂꢆꢄꢄꢄꢅꢂSꢉꢂꢇꢆꢄꢉꢂꢂ 3URFHGꢍꢀ,QWꢉꢅꢂꢇꢑꢑꢑꢅꢂYROꢉꢂꢃꢇꢅꢂSꢉꢂꢇꢇꢆꢉꢂꢂ
ꢆꢏꢉꢂ+DMLSRXUꢅꢂ $ꢉ5ꢉꢅꢂ 0DOODNSRXUꢅꢂ 6ꢉ(ꢉꢅꢂ DQGꢂ .KRHHꢅꢂ 6ꢉꢅꢂ ꢃꢆꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢅꢂ%DOWRUNꢅꢂ,ꢉ0ꢉꢅꢂDQGꢂ1LNQDPꢅꢂ.ꢉꢅꢂ2UJꢍꢀ
6\QOHWWꢅꢂꢆꢄꢄꢄꢅꢂSꢉꢂꢐꢁꢄꢉꢂ 3UHSꢍꢀ3URFHGꢍꢀ,QWꢉꢅꢂꢇꢑꢑꢑꢅꢂYROꢉꢂꢃꢇꢅꢂSꢉꢂꢃꢃꢎꢉꢂꢂ
ꢆꢐꢉꢂ%DOWRUNꢅꢂ,ꢉ0ꢉꢅꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢅꢂDQGꢂ 0RKDPPDGLꢅꢂ+ꢉꢅꢂ ꢃꢃꢉꢂ%DOWRUNꢅꢂ ,ꢉ0ꢉꢅꢂ +DMLSRXUꢅꢂ $ꢉ5ꢉꢅꢂ DQGꢂ +DGGDGLꢅꢂ 5ꢉꢅꢂꢂ
%XOOꢍꢀ&KHPꢍꢀ6RFꢍꢀ-SQꢉꢅꢂꢇꢑꢑꢀꢅꢂYROꢉꢂꢐꢇꢅꢂSꢉꢂꢇꢏꢉꢂꢂ -ꢍꢀ&KHPꢍꢀ5HVꢍꢁꢀ6\QRSꢉꢅꢂꢇꢑꢑꢑꢅꢂSꢉꢂꢇꢄꢆꢉꢂꢂ
ꢆꢀꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢂDQGꢂ0DKERRENKDKꢅꢂ1ꢉꢅꢂ6\QWKꢍꢀ&RPPXQꢉꢅꢂ ꢃꢁꢉꢂ+DMLSRXUꢅꢂ$ꢉ5ꢉꢅꢂ0DOODNSRXUꢅꢂ6ꢉ(ꢉꢅꢂDQGꢂ6DPLPLꢅꢂ+ꢉ$ꢉꢅꢂ
ꢇꢑꢑꢀꢅꢂYROꢉꢂꢆꢀꢅꢂSꢉꢂꢃꢇꢁꢃꢉꢂꢂ 6\QOHWWꢅꢂꢆꢄꢄꢇꢅꢂSꢉꢂꢇꢐꢃꢎꢉꢂ
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
ꢂ
ꢀ
ꢂ
ꢂ
ꢂ
ꢂ
5
866,$1ꢂꢂ-2851$/ꢂꢂ2)ꢂꢂ25*$1,&ꢂꢂ&+(0,675<ꢂꢂꢂ9ROꢉꢂꢂꢁꢆꢂꢂꢂ1Rꢉꢂꢂꢏꢂꢂꢂꢆꢄꢄꢏꢂ