Date of Award

Winter 2014

Publication Type

Master Thesis

Degree Name



Chemistry and Biochemistry

First Advisor

Wang, Zhuo


Organic chemistry




Bis-bispidine based tetraazamacrocycles can be used to encapsulate metal ions selectively to form highly stable complexes which may have interesting optical and electronic properties. This thesis discusses an effective synthetic pathway which has been used to obtain the desired bis-bispidine-based tetraazamacrocycles (Chapter 2). The synthesis of the macrocycles utilizes N -Boc- N -allylbispidinone 4 as the starting material which was subsequently converted to diketal bis(chloroacetamide) 8 and diketal bis(iodoacetamide) 9 . Cyclization of diketal bispidine hydrochloride 7 and bis(iodoacetamide) 9 followed by reduction afforded diketal bis-bispidine tetraazamacrocycle 12 . Cleavage of the ketal groups afforded a versatile bis-bispidinone substrate 13 which was further functionalized to diester 16 and bis-bispidine 17 . The desired bis-bispidine tetraazamacrocycle 17 was also obtained through another synthetic pathway which is discussed in Chapter 2. All the new compounds have been characterized by 1 H, 13 C NMR, IR, mass spectrometry and some by single crystal X-ray diffraction technique. Bis-bispidine-based tetraazamacrocycles have been used for coordination studies with metal ions under different reaction conditions and this is discussed in Chapter 3.