TY - JOUR
T1 - Trace amounts of second metal elements can play a key role in the generation of organometallic compounds
AU - Takai, Kazuhiko
N1 - Publisher Copyright:
© 2015 The Chemical Society of Japan.
PY - 2015
Y1 - 2015
N2 - During the development of new synthetic organic reactions by the use of group 47 metals, we twice encountered a reproducibility problem. The key factor was trace amounts of second metal elements that contaminated the first, main metals, i.e., nickel in chromium and lead in zinc. We had determined the standard procedures for these reactions and they were adopted in Organic Syntheses. The difference in the source of zinc, i.e., contamination by a catalytic amount of lead, proved to affect both the reactivity of the SimmonsSmith reaction and the formation of alkylzinc from the corresponding iodides. By using the concept of catalytic effects of the second metals, we developed a method to use manganese metal and applied this to sequential radical and anionic reactions. In addition, allylic aluminum species were prepared smoothly from allylic halides and aluminum by addition of an indium salt, the second element. In this account, I describe how the synthetic methods were discovered and developed, with an emphasis on the stories behind the communications and articles.
AB - During the development of new synthetic organic reactions by the use of group 47 metals, we twice encountered a reproducibility problem. The key factor was trace amounts of second metal elements that contaminated the first, main metals, i.e., nickel in chromium and lead in zinc. We had determined the standard procedures for these reactions and they were adopted in Organic Syntheses. The difference in the source of zinc, i.e., contamination by a catalytic amount of lead, proved to affect both the reactivity of the SimmonsSmith reaction and the formation of alkylzinc from the corresponding iodides. By using the concept of catalytic effects of the second metals, we developed a method to use manganese metal and applied this to sequential radical and anionic reactions. In addition, allylic aluminum species were prepared smoothly from allylic halides and aluminum by addition of an indium salt, the second element. In this account, I describe how the synthetic methods were discovered and developed, with an emphasis on the stories behind the communications and articles.
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U2 - 10.1246/bcsj.20150170
DO - 10.1246/bcsj.20150170
M3 - Article
AN - SCOPUS:84955253207
VL - 88
SP - 1511
EP - 1529
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
SN - 0009-2673
IS - 11
ER -