Studies on rearrangements in derivatives of grandiflorenic acid. Part 1. Reaction of the epoxides of methyl (–)-kaur-9(11)-en-19-oate and (–)-kaur-9(11)-en-19-oic acid with boron trifluoride-diethyl ether either in the absence or in the presence of N-nitrosomethylurea. Formation of two diterpenes of a new skeletal type

1985 ◽  
pp. 1693-1697 ◽  
Author(s):  
Tatsuhiko Nakano ◽  
Antonieta Castaldi Spinelli ◽  
Alfonso Martín ◽  
Alfredo Usubillaga ◽  
Andrew T. McPhail ◽  
...  
Keyword(s):  
Diethyl Ether ◽  
Boron Trifluoride ◽  
Derivatives Of

Boron Trifluoride-assisted Reactions of 1-Benzothiophen-3(2H)-one with Various Ketones: A Convenient Entry to 2-Methylene-1 -benzothiophen-3(2H)-one and/or 6H-Di[1]benzothieno[3,2-b:2,3-e]pyran Derivatives

1999 ◽  
Vol 23 (9) ◽  
pp. 542-543
Author(s):  
Alessandro Fraleoni ◽  
Paolo Zanirato
Keyword(s):  
Diethyl Ether ◽  
Boron Trifluoride ◽  
Room Temperature ◽  
Steric Factors ◽  
High Yields

The title compounds are obtained in moderate to high yields by BF3-assisted reaction of 1-benzothiophen-3(2 H)-one with nine ketones in diethyl ether at room temperature; the relative amounts of pyran 1 and ylidene 2 prove to be dependent upon electronic and steric factors.

Aminocyclitols. II. Synthesis of thioanalogues of 2,5-dideoxystreptamine

1978 ◽  
Vol 56 (21) ◽  
pp. 2743-2749 ◽  
Author(s):  
Gerry Kavadias ◽  
Robert Droghini
Keyword(s):  
Thionyl Chloride ◽  
Boron Trifluoride ◽  
Protective Groups ◽  
Thiobenzoic Acid ◽  
Derivatives Of ◽  
L 13

N,N′-Dibenzoyl-2,5-dideoxystreptamine (8b) reacted with thionyl chloride to form the bisoxazoline 9 and the latter compound was treated with thiobenzoic acid to produce the dithiobenzoate 10a. Removal of the protective groups in 10a afforded (l,3/4,6)-4,6-diamino-1,3-cyclohexanedithiol (1) dihydrochloride. Reaction of 8b with triethyl orthoacetate in the presence of boron trifluoride yielded the monooxazoline 12 which, on reaction with thiobenzoic acid followed by deprotection of the resulting 13a, afforded (d,l)-(13/4,6)-4,6-diamino-3-hydroxycyclohexanethiol (2) dihydrochloride. Similarly, 3-N-benzoyl-1-N-ethoxycarbonyl-2,5-dideoxystreptamine (15) and l-N-benzoyl-3-N-ethoxycarbonyl-2,5-dideoxystreptamine (20) were converted via their respective oxazolines 17a and 22a, to the enantiomeric aminothiols 3 and 4. Protected derivatives of 1–4 are also described.

Facile Conversion of Arenediazonium Salts to the Corresponding Fluoroarenes Using Boron Trifluoride Diethyl Ether Complex

1993 ◽  
Vol 23 (11) ◽  
pp. 1577-1582 ◽  
Author(s):  
Kojchi Shinhama ◽  
Shinji Aki ◽  
Takuya Furuta ◽  
Jun-ichi Minamikawa
Keyword(s):  
Diethyl Ether ◽  
Boron Trifluoride ◽  
Arenediazonium Salts ◽  
Ether Complex
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