Tetrahedron Letters

Design and reactivity of organic functional groups: the highly crystalline 2-alkoxy N, N′-diphenyl-1, 3, 2-diazaphospholanes and their facile conversion into alkyl …

S Hanessian, Y Leblanc, P Lavallée

Index: Hanessian, Stephen; Leblanc, Yves; Lavallee, Pierre Tetrahedron Letters, 1982 , vol. 23, # 43 p. 4411 - 4414

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Citation Number: 8

Abstract

Abstract Functionalization of alcohols as 2-alkoxy N, N′-diphenyl-1, 3, 2- diazaphospholanes affords highly crystalline derivatives useful for characterization purposes. These tervalent phosphorus derivatives undergo facile and mild conversion into the corresponding alkyl halides with inversion of configuration.

 Related Synthetic Route
2-(neopentyloxy)-1,3-diphenyl-1,3,2-diazaphospholidine Structure

85558-04-9

2-(neopentyloxy...

~29%

Neopentyl bromide Structure

630-17-1

Neopentyl bromide

2-(((1R,2R,4S)-bicyclo[2.2.1]heptan-2-yl)oxy)-1,3-diphenyl-1,3,2-diazaphospholidine Structure

85557-99-9

2-(((1R,2R,4S)-...

~%

exo-norborneol Structure

497-37-0

exo-norborneol

2-(((1R,2R,4S)-bicyclo[2.2.1]heptan-2-yl)oxy)-1,3-diphenyl-1,3,2-diazaphospholidine Structure

85557-99-9

2-(((1R,2R,4S)-...

~%

rel-(1R,2S,4S)-norbornan-2-ol Structure

497-36-9

rel-(1R,2S,4S)-...

2-(((1R,2R,4S)-bicyclo[2.2.1]heptan-2-yl)oxy)-1,3-diphenyl-1,3,2-diazaphospholidine Structure

85557-99-9

2-(((1R,2R,4S)-...

~78%

EXO-2-BROMONORBORNANE Structure

2534-77-2

EXO-2-BROMONORB...

1-Octanol Structure

111-87-5

1-Octanol

dimethylamino-2,N,N' diphenyl-1,3 diazaphospholane-1,3,2 Structure

81106-32-3

dimethylamino-2...

~72%

1-Iodooctane Structure

629-27-6

1-Iodooctane

2-(((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)-1,3-diphenyl-1,3,2-diazaphospholidine Structure

85558-05-0

2-(((3aR,4R,6R,...

~%

((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol Structure

4099-85-8

((3aR,4R,6R,6aR...

1,3-diphenyl-2-(((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)methoxy)-1,3,2-diazaphospholidine Structure

85597-20-2

1,3-diphenyl-2-...

~81%

1,2:3,4-Di-O-isopropyliden- 6-deoxy-6-bromo-alpha-D-galactopyranose Structure

38838-08-3

1,2:3,4-Di-O-is...

1,3-diphenyl-2-(((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)methoxy)-1,3,2-diazaphospholidine Structure

85597-20-2

1,3-diphenyl-2-...

~91%

5-(iodomethyl)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydro-3aH-di[1,3]dioxolo[4,5-a:5',4'-d]pyran Structure

4026-28-2

5-(iodomethyl)-...

2-(((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)-1,3-diphenyl-1,3,2-diazaphospholidine Structure

85558-05-0

2-(((3aR,4R,6R,...

~70%

(3aS,4S,6R,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole Structure

38838-06-1

(3aS,4S,6R,6aR)...

2-Nonanol Structure

628-99-9

2-Nonanol

dimethylamino-2,N,N' diphenyl-1,3 diazaphospholane-1,3,2 Structure

81106-32-3

dimethylamino-2...

~%

Nonane, 2-bromo- Structure

2216-35-5

Nonane, 2-bromo-


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