Abstract
Conrotatory ring opening of cyclobutene, 3-methoxycyclobutene, and 3-formylcyclobutene has been studied with the density functional theory. The stereoselectivity of these reactions has been elucidated on the basis of the natural bond orbital analysis and correlation diagrams. Hyperconjugative interactions substituent-cyclobutene occurring at the transition state seem to be responsible of these reactions' torquoselectivity.
Get full access to this article
View all access options for this article.
References
1.
Kirmse
W.
,
Rondan
N.G.
and
Houk
K.N.
, J. Am. Chem. Soc. 106 (1984 ), 7989 .
2.
Curry
M.J.
and
Stevens
I.D.R.
, J. Chem. Soc., Perkin Trans. 1 409 (1974 ), 415 .
3.
Dolbier Jr.
W.R.
,
Koroniak
H.
,
Burton
D.J.
,
Bailey
A.R.
,
Shaw
G.S.
and
Hansen
S.W.
, J. Am. Chem. Soc. 106 (1984 ), 1871 .
4.
Frey
H.M.
,
Pope
B.M.
and
Skinner
R.F.
, Trans. Faraday Soc. 63 (1967 ), 1166 .
5.
Rondan
N.G.
and
Houk
K.N.
, J. Am. Chem. Soc. 107 (1985 ), 2099 .
6.
Lopez
S.A.
and
Houk
K.N.
, J. Org. Chem. 79 (2014 ), 6189 .
7.
Jaccob
M.
,
Sheeba
J.
,
Giri
S.
,
Venuvanalingam
P.
and
Chattaraj
P.K.
, J. Phys. Org. Chem. 24 (2011 ), 460 .
8.
Mori
S.
and
Shindo
M.
, Org. Lett. 6 (2004 ), 3945 .
9.
Yoshikawa
T.
,
Mori
S.
and
Shindo
M.
, J. Am. Chem. Soc. 131 (2009 ), 2092 .
10.
Honda
K.
,
Lopez
S.A.
,
Houk
K.N.
and
Mikami
K.
, J. Org. Chem. 80 (2015 ), 11768 .
11.
Banks
H.D.
, J. Org. Chem. 75 (2010 ), 2510 .
12.
Nakamura
K.
and
Houk
K.N.
, Heterocycles 35 (1993 ), 631 .
13.
Niwayama
S.
,
Kallel
A.E.
,
Sheu
C.
and
Houk
K.N.
, J. Org. Chem. 61 (1996 ), 2517 .
14.
Evanseck
J.D.
,
Thesis
, University of Californa, Los Angeles, 1990 .
15.
Faza
O.N.
,
Lpez
C.S.
,
Álvarez
R.
and
de Lera
Á.R.
, J. Org. Chem. 69 (2004 ), 9002 .
16.
Faza
O.N.
,
Lpez
C.S.
,
Gonzalez-Perez
A.B.
,
Perez-Rodriguez
M.
and
de Lera
ÁR.
, J. Phys. Org. Chem. 22 (2009 ), 378 .
17.
Thomas
B.E.
,
Evanseck
IV, J.D.
and
Houk
K.N.
, J. Am. Chem. Soc. 115 (1993 ), 4165 .
18.
Dolbier Jr.
W.R.
,
Koroniak
H.
,
Houk
K.N.
and
Sheu
C.
, Acc. Chem. Res. 29 (1996 ), 471 .
19.
Foster
J.P.
and
Weinhold
F.
, J. Am. Chem. Soc. 102 (1980 ), 7211 .
20.
Reed
A.E.
and
Weinhold
F.
, J. Chem. Phys. 78 (1983 ), 4066 .
21.
Reed
A.E.
,
Weinstock
R.B.
and
Weinhold
F.
, J. Chem. Phys. 83 (1985 ), 735 .
22.
Reed
A.E.
and
Weinhold
F.
, J. Chem. Phys. 83 (1985 ), 1736 .
23.
Carpenter
J.E.
and
Weinhold
F.
, J. Mol. Struct. (Theochem) 46 (1988 ), 41 .
24.
Reed
A.E.
,
Curtiss
L.A.
and
Weinhold
F.
, Chem. Rev. 88 (1988 ), 899 .
25.
Yoshikawa
T.
,
Mori
S.
and
Shindo
M.
, Tetrahedron 65 (2009 ), 8832 .
26.
Akilandeswari
L.
and
Prathipa
C.
, J. Chem. Sci. 127 (2015 ), 1505 .
27.
Choo
J.
,
Kim
S.
,
Joo
H.
and
Kwon
Y.
, J. Mol. Struct. (Theochem) 587 (2002 ), 1 .
28.
Faza
O.N.
,
Lpez
C.S.
,
Álvarez
R.
and
de Lera
Á.R.
, Chem. Eur. J. 15 (2009 ), 1944 .
29.
Shindo
M.
, Tetrahedron 63 (2007 ), 10 .
30.
Murakami
M.
,
Miyamoto
Y.
,
Hasegawa
M.
,
Usui
I.
and
Matsuda
T.
, Pure Appl. Chem. 78 (2006 ), 415 .
31.
Murakami
M.
and
Hasegawa
M.
, Angew. Chem. Int. Ed. 43 (2004 ), 4874 .
32.
Murakami
M.
,
Hasegawa
M.
and
Igawa
H.
, J. Org. Chem. 69 (2004 ), 587 .
33.
Faza
O.N.
,
Lpez
C.S.
,
Álvarez
R.
and
de Lera
Á.R.
, Org. Lett. 6 (2004 ), 901 .
34.
Carr Jr.
R.W.
and
Walters
W.D.
, J. Phys. Chem. 69 (1965 ), 1073 .
35.
Sarner
S.F.
,
Gale
D.M.
,
Hall Jr.
H.K.
and
Richmond
A.B.
, J. Phys. Chem. 76 (1972 ), 2817 .
36.
Zhao
Y.
,
Schultz
N.E.
and
Truhlar
D.G.
, J. Chem. Theory Comput. 2 (2006 ), 364 .
37.
Foresman
J.B.
and
Frisch
Æ.
,
Exploring Chemistry with Electronic Structure Methods
, 2nd Ed. Gaussian, In. Pittsburgh , PA. 1996 ; pp. 141 -162 .
38.
Dunning Jr.
T.H.
, J. Chem. Phys. 90 (1989 ), 1007 .
39.
Frisch
M.J.
,
Trucks
G.W.
,
Schlegel
H.B.
,
Scuseria
G.E.
,
Robb
M.A.
,
Cheeseman
J.R.
,
Scalmani
G.
,
Barone
V.
,
Mennucci
B.
,
Petersson
G.A.
,
Nakatsuji
H.
,
Caricato
M.
,
Li
X.
,
Hratchian
H.P.
,
Izmaylov
A.F.
,
Bloino
J.
,
Zheng
G.
,
Sonnenberg
J.L.
,
Hada
M.
,
Ehara
M.
,
Toyota
K.
,
Fukuda
R.
,
Hasegawa
J.
,
Ishida
M.
,
Nakajima
T.
,
Honda
Y.
,
Kitao
O.
,
Nakai
H.
,
Vreven
T.
,
Montgomery Jr.
J.A.
,
J.E. Peralta
,
Ogliaro
F.
,
Bearpark
M.
,
Heyd
J.J.
,
Brothers
E.
,
Kudin
K.N.
,
Staroverov
V.N.
,
Keith
T.
,
Kobayashi
R.
,
Normand
J.
,
Raghavachari
K.
,
Rendell
A.
,
Burant
J.C.
,
Iyengar
S.S.
,
Tomasi
J.
,
Cossi
M.
,
Rega
N.
,
Millam
J.M.
,
Klene
M.
,
Knox
J.E.
,
Cross
J.B.
,
Bakken
V.
,
Adamo
C.
,
Jaramillo
J.
,
Gomperts
R.
,
Stratmann
R.E.
,
Yazyev
O.
,
Austin
A.J.
,
Cammi
R.
,
Pomelli
C.
,
Ochterski
J.W.
,
Martin
R.L.
,
Morokuma
K.
,
Zakrzewski
V.G.
,
Voth
G.A.
,
Salvador
P.
,
Dannenberg
J.J.
,
Dapprich
S.
,
Daniels
A.D.
,
Farkas
O.
,
Foresman
J.B.
,
Ortiz
J.V.
,
J.Cioslowski
and
J. Fox
D.
, Gaussian 09, Revision C.01 , Gaussian, Inc., Wallingford CT, 2010 .
40.
Morales-Bayuelo
A.
,
Pan
S.
,
Caballero
J.
and
Chattaraj
P.K.
, Phys. Chem. Chem. Phys. 17 (2015 ), 23104 .