Synthesis and Properties of Naphtho[2,3-e]-1,2-azaphosphorine 2-Oxides: PN-Anthracene Analogues

被引：14

作者：

Takaesu, Noah A. ^{[1
,2
]}

Ohta, Eisuke ^{[1
,2
,4
]}

Zakharov, Lev N. ^{[3
]}

Johnson, Darren W. ^{[1
,2
]}

Haley, Michael M. ^{[1
,2
]}

机构：

[1] Univ Oregon, Dept Chem & Biochem, Eugene, OR 97403 USA

[2] Univ Oregon, Inst Mat Sci, Eugene, OR 97403 USA

[3] Univ Oregon, CAMCOR, Eugene, OR 97403 USA

[4] Osaka Prefecture Univ, Dept Appl Chem, Grad Sch Engn, Naka Ku, 1-1 Gakuen Cho, Sakai, Osaka 5998531, Japan

来源：

ORGANOMETALLICS | 2017年 / 36卷 / 14期

基金：

美国国家科学基金会;

关键词：

HETEROCYCLIC PHOSPHORUS-COMPOUNDS; STEREOCHEMISTRY; CYCLIZATION;

D O I：

10.1021/acs.organomet.7b00281

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

We report the expedient synthesis of a series of new "PN-anthracene" derivatives, the naphtho[2,3-e]-1,2-azaphosphorine-2-oxides, which incorporate a variety of 3-aryl substituents. These compounds represent a new class of pi-extended PN-heterocycles, featuring strong UV absorption, emission in the visible range, and Stokes shifts up to 10000 cm(-1). These molecules show alignment of dipoles, strong dimerization through N-H and P=O hydrogen bond donors/acceptors, and efficient aromatic stacking in the solid state.

引用

页码：2491 / 2493

页数：3

共 50 条

[21] STRUCTURES OF 3-CYANOHEXAHYDRONAPHTH[2,3-E][1,2]OXAZINES .2.
HOLZAPFEL, CW
KRUGER, GJ
VANDYK, MS
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1987, 43 : 598 - 601
[22] SYNTHESIS AND REACTIONS OF 1,2-BENZOXATHIAN-4-ONE 2-OXIDES
BARBIERI, W
BERNARDI, L
CODA, S
VIGEVANI, A
TETRAHEDRON LETTERS, 1971, (52) : 4913 - &
[23] Synthesis of 2-substituted-2,3-dihydro-3-(2-nitrophenyl)-1H-naphth[1,2-e] [1,3,2]oxazaphosphorine 2-oxides
Venugopal, M
Reddy, CD
Raju, CN
Berlin, KD
HETEROCYCLIC COMMUNICATIONS, 2000, 6 (03) : 253 - 258
[24] Reaction of 2-R-naphtho[2,3-d][1,3,2]dioxaphosphinin-4-ones with arylidene derivatives of malonic acid esters: synthesis, molecular and crystal structures of 5-oxo-2-R-naphtho[2,3-f][1,2]oxaphosphepine 2-oxides
V. F. Mironov
G. A. Ivkova
M. N. Dimukhametov
Sh. K. Latypov
I. A. Litvinov
Russian Chemical Bulletin, 2023, 72 : 997 - 1011
[25] Reaction of 2-R-naphtho[2,3-d][1,3,2]dioxaphosphinin-4-ones with arylidene derivatives of malonic acid esters: synthesis, molecular and crystal structures of 5-oxo-2-R-naphtho[2,3-f][1,2]oxaphosphepine 2-oxides
Mironov, V. F.
Ivkova, G. A.
Dimukhametov, M. N.
Latypov, Sh. K.
Litvinov, I. A.
RUSSIAN CHEMICAL BULLETIN, 2023, 72 (04) : 997 - 1011
[26] 2,3-DIHYDRONAPHTHO[1,2-B]THIOPHEN-1-OXIDES IN THE SYNTHESIS OF 2,3-DIHYDRONAPHTHO[1,2-B]THIOPHENES AND NAPHTHO[1,2-B]THIOPHENES
FEDOROV, NV
ANISIMOV, AV
VIKTOROVA, EA
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1989, (12): : 1629 - 1633
[27] A NOVEL PRACTICAL SYNTHESIS OF PYRROLO[1,2-A]THIENO[2,3-E][1,4]DIAZEPINES
DAICH, A
MOREL, J
DECROIX, B
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (03) : 675 - 678
[28] SYNTHESIS AND PROPERTIES OF PYRIDO[2,3-E]-1,2,4-THIADIAZINE-1,1-DIOXIDES
KOTOVSKAYA, SK
MOKRUSHINA, GA
POSTOVSKY, IY
PIDEMSKY, EL
GOLENEVA, AF
VYSOKOVA, TY
KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1979, 13 (04): : 54 - 57
[29] EFFICIENT SELENATION OF QUINONES - SYNTHESIS OF NOVEL BENZO[B]NAPHTHO[2,3-E]SELENINTRIONE AND DIBENZO[B,E]SELENINONE
SAKAKIBARA, M
TORU, T
IMAI, T
WATANABE, Y
UENO, Y
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (05) : 1291 - 1294
[30] Synthesis and antimicrobial activity of 3-(N-arylamino)-2-phenyl-naphtho[1,3-d]-1,2-oxaphosphole 2-oxides
Haranath, P
Anasuyamma, U
Raju, CN
Reddy, CD
Reddy, CS
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (05) : 775 - 779

← 1 2 3 4 5 →