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. Author manuscript; available in PMC: 2014 Jan 18.
Published in final edited form as: ACS Comb Sci. 2012 Sep 18;14(10):558–564. doi: 10.1021/co3000852

Table 1.

Cyclic six-membered ring formation (%) with respect to the expected chain elongation product.

R Amine Cyclic product (%)
Ph Isopropyl amine 63
CH2Ph Isopropyl amine ND
OCH2Ph Isopropyl amine ND
NHPh Isopropyl amine ND
4-OMe-Ph 2-methoxyethyl amine 4
4-Br-Ph 2-methoxyethyl amine 15
4-Cl-Ph 2-methoxyethyl amine 16
4-NO2-Ph 2-methoxyethyl amine 45
3-F-Ph 2-methoxyethyl amine 15
Thiophene 2-methoxyethyl amine 10
Furan 2-methoxyethyl amine 6
CH2CH2CH2CH3 2-methoxyethyl amine ND
CH3 2-methoxyethyl amine ND

ND-not detected based on MALDI MS and HPLC of crude reaction mixture