NITRATION BY OXIDES OF NITROGEN .7. PREPARATION OF DINITRATES AND POLYNITRATES BY RING-OPENING NITRATION OF OXETANES BY DINITROGEN PENTOXIDE (N2O5)

被引：20

作者：

GOLDING, P ^{[1
]}

MILLAR, RW ^{[1
]}

PAUL, NC ^{[1
]}

RICHARDS, DH ^{[1
]}

机构：

[1] DEF RES AGCY,FT HALSTEAD,SEVENOAKS TN14 7BP,KENT,ENGLAND

来源：

TETRAHEDRON | 1993年 / 49卷 / 32期

关键词：

D O I：

10.1016/S0040-4020(01)87979-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ten oxetanes bearing various substituents were reacted with N2O5 in chlorinated hydrocarbon solvents to yield 1,3-dinitrate esters (I) by ring-opening nitration. The yields ranged from 73 to 88% for di-/trinitrates derived from oxetanes unsubstituted in the 2-position, to only 15 to 21% for oxetanes bearing such substituents. Although selective ring cleavage of oxetanes bearing non-hydroxylic substituents (epoxy (oxiranyl), spiro-oxetane and alkene) was not, in general, possible, selective nitration of hydroxyalkyloxetanes was achievable under the conditions employed to yield nitrato-methyloxetanes useful as precursors for energetic polyethers. A semi-quantitative reactivity comparison with representative epoxides indicated that the reactivity of oxetanes towards N2O5 was lower, as expected on account of their lower ring strain.

引用

页码：7051 / 7062

页数：12

共 21 条

[11]

Katritzky A R, 1985, HDB HETEROCYCLIC CHE, P132

[12]

Manser G. E, 1984, Energetic Copolymers and method of making same, Patent No. [4,483,978, 4483978]

[13]

Manser G. E., 1983, Patent, pA, Patent No. [US 4393199, 4393199]

[14]

MILLAR RW, UNPUB

[15]

ODEH AMS, 1980, HETEROCYCLES, V14, P189

[16]

PARTINGTON JR, 1949, GENERAL INORGANIC CH, P562

[17]

PICARD P, 1981, SYNTHESIS-STUTTGART, P550

[18]

SEARLES S, 1964, CHEM HETEROCYCLIC 2, P983

[19] THE DINITROGEN PENTOXIDE-OLEFIN REACTION [J].

STEVENS, TE ;

EMMONS, WD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (22) :6008-6014

[20]

STEWART M, 1990, 21ST P ANN C ICT TEC

← 1 2 3 →