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Synthesis and reactivity of 3‐(trichlorogermyl)propanoic acid and 3‐(triphenylgermyl) propanoic acid
Author(s) -
Qiang Zeng,
XianShun Zeng,
QingMin Wang,
Tao Cui,
ZhongBiao Zhang
Publication year - 1998
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19980160212
Subject(s) - phenylmagnesium bromide , chemistry , propanoic acid , hydrochloric acid , carbamate , bromide , organic chemistry , medicinal chemistry , reagent
3‐(Trichlorogermyl)propanoic acid (1a) reacts with phenylmagnesium bromide in molar ratio 1:4 to give 3‐(triphenylgermyl)propanoic acid (2a). In the compounds 1a and 2a the β ‐carboxylic functional group shows some unusual properties when they react with excess of phenylmagnesium bromide. The compound 1a reacts with phenylmagnesium bromide in molar ratio 1:5 to give phenyl 2‐(triphenylgermyl)ethylketone (3a) and in molar ratio 1:6 to give 1,1‐diphenyl‐3–(triphenylgermyl)propanol (4a). The compound 2a reacts with phenylmagnesium bromide in molar ratio 1:2 to give 3a and in molar ratio 1:3 to give 4a also. Dehydration of the compound 4a with dilute hydrochloric acid seems especially easy. Moreover, the compound la reacted with phenylmagnesium bromide in molar ratio 1:6, then the mixture was treated with dilute hydrochloric acid to give 1,1‐diphenyl‐3 (triphenylgermyl)‐1‐propene (5a) in one pot reaction. Alkyl Ge–C bond in the compound 5a can be cleaved selectively by lithium aluminium hydride (LiAlH 4 ) in good yield.