OAC Group Research Articles

Organoboron compounds. 367. Mass-spectrometric study of the inner complexes of 3-aminopropyldialkylboranes and some of their derivatives

1. The principal dissociation route of the molecular ions of the inner complex 3-aminopropyldialkylboranes and 3-cyclohexyldeneaminopropyldialkylboranes is the splitting off of the alkyl groups on the boron with formation of ions of the type (M-R)+ and [(M-R) —(R1−H)]+. 2. For acyloxy- or hydroxy(3-aminopropyl)alkylboranes, besides splitting off of an alkyl group, the cleavage of an AcOH or H2O molecule respectively was a characteristic feature. For N-disubstituted compounds possessing an OH, Cl, or OAc group in addition to an alkyl group on the boron atom, the alkyl group was predominantly split off from the M+. ion.

ChemInform Abstract: THE REACTIONS OF CARBONIMIDOYL DICHLORIDES WITH METAL THIOACETATES, ACETATES, THIOCYANATES, AND SELENOCYANATE

AbstractUmsetzung des Carbonimidoylchlorids (I) mit K‐ bzw. Tl‐thioacetat (IIb) wie auch mit KSCN (IV) liefert jeweils ausschließlich das Isothiocyanat (III); analog entsteht aus (I) und KSeCN das Isoselenocyanat (IV).

ChemInform Abstract: CYCLIZATION OF POLYENES. XXI. SYNTHESIS OF DL‐INCENSOLE

AbstractD,L‐Mukulol (I) reagiert mit dem Tetrabromcyclohexadienon (II) zu einem Bromäther (III), aus dem in bekannter Weise das D,L‐Incensol (IV) entsteht.

The Reactions of Carbonimidoyl Dichlorides with Metal Thioacetates, Acetates, Thiocyanates, and Selenocyanate

Abstract The reactions of carbonimidoyl dichlorides with potassium thioacetate and thiocyanate in tetrahydrofuran afford the corresponding isothiocyanates. Similarly, the reaction with potassium selenocyanate gives isoselenocyanates. Thallium (I) acetate reacts with phenylcarbonimidoyl dichloride with greater facility than potassium acetate to give a mixture of phenyl isocyanate and acetanilide in which the latter is predominant. A displacement of one chlorine atom in the carbonimidoyl dichlorides by a SAc, OAc, SCN, or SeCN group, followed by elimination of AcCl or CNCl, has been proposed as a reasonable reaction path.

CYCLIZATION OF POLYENES XXI. SYNTHESIS OF Dl-INCENSOLE

Abstract By treatment of dl-mukulol (III) with tetrabromocyclohexadienone (V, TBCO), bromo ether (VI) was obtained. The ether (VI) was converted to dl-incensole (IV) by the sequential reactions of isomerization with BF3-etherate, replacement of bromine atom of VII with OAc group followed by reduction with LiAlH4.