TY - JOUR
T1 - A Transient Vinylphosphinidene via a Phosphirene-Phosphinidene Rearrangement
AU - Liu, Liu Leo
AU - Zhou, Jiliang
AU - Cao, Levy L.
AU - Andrews, Ryan
AU - Falconer, Rosalyn L.
AU - Russell, Christopher A.
AU - Stephan, Douglas W.
PY - 2018/1/10
Y1 - 2018/1/10
N2 - A room-temperature-stable crystalline 2H-phosphirene (1) was prepared by treatment of an electrophilic diamidocarbene with tert-butylphosphaalkyne. Compound 1 is shown to react as a vinylphosphinidene generated via phosphirene-phosphinidene rearrangement. Thermolysis is shown to affect C-N bond scission while reactions with C6Cl4O2 or (tht)AuCl afford formal oxidation of the phosphindene center and the phosphinidene-insertion into an aromatic C-C bond of a mesityl group, respectively. The latter reaction is the first example of a phosphorus analog of the Büchner ring expansion reaction.
AB - A room-temperature-stable crystalline 2H-phosphirene (1) was prepared by treatment of an electrophilic diamidocarbene with tert-butylphosphaalkyne. Compound 1 is shown to react as a vinylphosphinidene generated via phosphirene-phosphinidene rearrangement. Thermolysis is shown to affect C-N bond scission while reactions with C6Cl4O2 or (tht)AuCl afford formal oxidation of the phosphindene center and the phosphinidene-insertion into an aromatic C-C bond of a mesityl group, respectively. The latter reaction is the first example of a phosphorus analog of the Büchner ring expansion reaction.
UR - http://www.scopus.com/inward/record.url?scp=85040325557&partnerID=8YFLogxK
UR - https://research-information.bristol.ac.uk/en/publications/a-transient-vinylphosphinidene-via-a-phosphirenephosphinidene-rearrangement(bc270929-86d1-4526-bc0b-803a533312a3).html
U2 - 10.1021/jacs.7b11791
DO - 10.1021/jacs.7b11791
M3 - Article
AN - SCOPUS:85040325557
SN - 0002-7863
VL - 140
SP - 147
EP - 150
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 1
ER -