Open AccessThe acetolysis of 2‐acetoxyalkyltellurium trihalides
Author(s) -
Miess Robert D.,
O'Brien Daniel H.
Publication year - 1998
Publication title -
heteroatom chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.283
H-Index - 42
eISSN - 1098-1071
pISSN - 1042-7163
DOI - 10.1002/(sici)1098-1071(1998)9:1<85::aid-hc11>3.0.co;2-z
Subject(s) - chemistry , tellurium , heteroatom , halide , acetic acid , sn2 reaction , walden inversion , lithium (medication) , medicinal chemistry , cleavage (geology) , acetic anhydride , ion , carbon fibers , organic chemistry , ring (chemistry) , catalysis , medicine , materials science , geotechnical engineering , fracture (geology) , composite number , engineering , composite material , endocrinology
The reaction of six 2‐acetoxyalkyltellurium trihalides in refluxing dry acetic acid yields haloacetates in addition to the previously observed diacetates. The haloacetates are formed either through direct cleavage of the carbon–tellurium bond with retention of configuration or through initial formation of a neighboring group intermediate that is subsequently attacked by halide ion. Added lithium acetate leads to an increase in S N 2 attack on the tellurium carbon. © 1998 John Wiley & Sons, Inc. Heteroatom Chem 9:85–93, 1998