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1-芳香基-2,2-二氯環丙烷化合物具高度環張力及電子密度，在進行硝化
反應後，可得異▌▌之開環產物﹔對含其他取代基之苯基環丙烷，如甲基
、氯甲基、苯環或是以 基取代苯基，進行硝化反應，來探討溫度及NO2+
與反應物之比例對產物分佈之影響，除了1-甲基-1-苯基-2,2-二鹵環丙烷
形成開環主產物 5-甲基-5-(4'-硝基苯)-3-鹵異▌▌▌外，其他六個環丙
烷化合物的產物皆以苯環上硝基取代為主之原因。另外，利用電腦輔助分
子模擬之理論計算—半經驗法，來探討一系列1-芳香基-2-鹵環丙烷的環
丙烷上三個碳原子之13C NMR SCS值、Hammett值與三種方法(MNDO,AM1,
PM3)之電荷密度的關係，並得到三種方法之電荷密度值皆可與1-芳香基環
丙烷之13C NMR SCS值、Hammett值相呼應，但 順-1-芳香基-2-溴環丙烷
之Cβ，1-芳香基-2,2-二氯環丙烷之Cβ、Cγ及1-芳香基-2,2-二溴環丙
烷之Cβ的13C NMR SCS值、 Hammett值，分別與 MNDO,AM1,PM3之電荷密
度值有較一致性的關係。
The high ring strain and high electron density of cyclopropanes
result in formation of isoxazoles from the ring opening during
the nitration of 1-aryl-2,2-dichlorocyclopropanes. The study of
phenylcyclopropanes contain an additional of substituents,such
as methyl, chloromethyl, phenyl or naphthyl group instead of
phenyl, were nitrated under various temperature and the ratio
between cyclopropane and HNO3 to investigate the effect on the
resultants. The major products from six cyclopropane are the
nitro substitution on phenyl, except for 2,2-dihalogeno-1-
methyl-1-phenylcyclopropane which yields 3-halogeno-5-
methyl-5-(4'-nitrophenyl)isoxazoline. In addition, the Semi-
Empirical method (MNDO,AM1,PM3) is applied for the calculation
of the charge densities of three carbons for the
cyclopropanes of 1-aryl-2-halogenocyclopropanes to study of the
correlation between SCS from 13C NMR chemical shift, Hammett
constant and charge densities from calculation. The charge
densities from three calculative methods are correlated to SCS
from 13C NMR and Hammett constant of 1-arylcyclopropanes. But
SCS from 13C NMR and Hammett constant of Cβ of cis-1-aryl-2-
bromocyclopropane, Cβ,Cγ of 1-aryl-2,2-dichlorocyclopropane, C
βof 1-aryl-dibromocyclopropane only are well correlated to the
charge densities from MNDO,AM1, PM3, respectively.
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